Oil materials comprising dimerdiol ester and cosmetics comprising the ester

ABSTRACT

An oil material comprising a dimerdiol ester with a monocarboxylic acid having 4 to 34 carbon atoms or with a dimerdiol ester with a dicarboxylic acid; and a cosmetic and an external agent excellent in safety, stability, gloss, feeling and the like comprising the dimerdiol carboxylate.

BACKGROUND OF THE INVENTION

The present invention relates to oil materials comprising an ester ofdimerdiol with monocarboxylic acid having 4 to 34 carbon atoms or anester of dimerdiol with dicarboxylic acid, and cosmetics and externalagents comprising the dimerdiol ester. More specifically, the presentinvention relates to oil materials comprising a dimerdiol carboxylateexcellent in safety, stability, gloss, feeling and the like, andcosmetics and external agents comprising the ester excellent in safety,stability, gloss, feeling and the like. (Hereinafter, “ester ofdimerdiol” is referred to as “dimerdiol ester”.)

DESCRIPTION OF THE RELATED ART

Conventionally, various esters and oil materials comprising the estershave been used in cosmetics and external agents. For example, cetylisooctanoate, isodecyl isononanoate, isopropyl palmitate, octyldodecylmyristate, octyl stearate, isostearyl isostearate, glycerylisooctanoate, glyceryl isostearate, octyldodecyl oleate, ethyllinoleate, ethyl cinnamate, octyl salicylate, propyl p-oxybenzoate,dioctyl phthalate, diisostearyl malate and the like are known. However,these esters are not necessarily satisfactory in safety, stability,gloss, feeling and the like as raw materials of cosmetics and externalagents. Therefore, there have been a desire for raw materials ofcosmetics excellent in safety, stability, gloss and feeling and furtherexcellent in hydrolysis resistance, pigment dispersing property, lessodor and the like.

The present inventors have intensively studied to solve theabove-mentioned problems. As a result, they have found that a dimerdiolester with a monocarboxylic acid having 4 to 34 carbon atoms, adimerdiol ester with a dicarboxylic acid and oil materials comprisingthe ester are excellent in safety, stability, gloss, feeling of use andthe like as a raw material of cosmetics and external agents. Thus, thepresent invention was completed.

SUMMARY OF THE INVENTION

The present invention provides an oil material comprising a dimerdiolester with a monocarboxylic acid having 4 to 34 carbon atoms or adimerdiol ester with a dicarboxylic acid.

The present invention further provides a cosmetic and an external agentexcellent in safety, stability, gloss, feeling and the like comprisingthe dimerdiol carboxylate.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The dimerdiols and/or esters thereof used for producing the dimerdiolcarboxylate and oils comprising the ester of the present invention areknown, and can be produced, for example, by hydrogen reduction ofindustrially obtainable dimer acids and/or esters thereof.

A dimer acid is a known dibasic acid obtainable by an intermolecularpolymerization reaction of an unsaturated fatty acid, and the industrialproduction process thereof is approximately standardized in the art. Forexample, a dimer acid and/or a lower alcohol ester thereof can beobtained by dimerization of an unsaturated fatty acid having 11 to 22carbon atoms and/or a lower alcohol ester thereof with a clay catalyst.

An industrially obtainable dimer acid is mainly composed of a dibasicacid having about 36 carbon atoms. It also contains a trimer acid andmonomer acid in any amount depending on the degree of purification. Ingeneral, those in which the content of a dimer acid is over 70 wt % andthose in which the content of a dimer acid has been increased to 90% ormore are commercially available. Further, those which oxidationstability has been improved by hydrogenation of double bonds remainingafter the dimerization reaction are also commercially available. In thepresent invention, any of dimer acids thus commercially available inpresent can be used.

An industrially obtainable dimerdiol contains other component, forexample, a trimer triol, monoalcohol, and ether compound, depending onthe degree of purification of a dimer acid and/or a lower alcohol esterthere of used as a raw material. In general, those in which the contentof a dimerdiol is over 70 wt % can be used in the present invention,although a high purity dimerdiol, such as a dimerdiol in which itscontent is over 90 wt %, is preferable.

A dimerdiol produced by hydrogenating a dimer acid obtained bydimerization of an unsaturated fatty acid having 11 to 22 carbon atomswith a clay catalyst usually contains 70 to 100 wt % of a diolcomponent. It is considered that the dimerdiol mainly contains compoundsrepresented by the following structural formula 1 and/or structuralformula 2:

wherein, each of m, n, p and q independently represents an integer andm+n+p+q is from 14 to 36;

wherein, each of r, s, t and u independently represents an integer andr+s+t+u is from 18 to 40.

The monocarboxylic acid used in the present invention is notparticularly restricted providing it has 4 to 34 carbon atoms,preferably 10 to 32 carbon atoms. Examples of the monocarboxylic acidused in the present invention include linear saturated acids such asbutanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoicacid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid,tridecanoic acid, tetradecanoic acid, heptadecanoic acid, hexadecanoicacid, pentadecanoic acid, octadecanoic acid, nonadecanoic acid,eicosanoic acid, docosanoic acid, tetracosanoic acid and the like;branched fatty acids such as isobutanoic acid, isopentanoic acid,pivalic acid, isohexanoic acid, isoheptanoic acid, isooctanoic acid,diemthyloctanoic acid, isononanoic acid, isodecanoic acid, isoundecanoicacid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid,isopentadecanoic acid, isohexadecanoic acid, isoheptadecanoic acid,isooctadecanoic acid, isononadecanoic acid, isoeicosanoic acid,2-ethylhexanoic acid, 2-butyloctanoic acid, 2-hexyldecanoic acid,2-octyldodecanoic acid, 2-decyltetradecanoic acid, 2-dodecylhexadecanoicacid, 2-tetradecyloctadecanoic acid, 2-hexadecyloctadecanoic acid, longchain fatty acids obtained from lanolin, and the like; linearunsaturated fatty acids having 8-34 carbon atoms such as undecenoicacid, linderic acid, myristoleic acid, palmitoleic acid, oleic acid,linoleic acid, linolenic acid, elaidinic acid, gadolenoic acid,eicosapentaenoic acid, docosahexaenoic acid, erucic acid, brassidicacid, arachidonic acid and the like; hydroxy acids such as2-hydrbxybutanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid,2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, 2-hydroxynonanoic acid,2-hydroxydecanoic acid, 2-hydroxyundecanoic acid, 2-hydroxydodecanoicacid, 2-hydroxytridecanoic acid, 2-hydroxytetradecanoic acid,2-hydroxyhexadecanoic acid, 2-hydroxyheptadecanoic acid,2-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid,2-hydroxynonadecanoic acid, 2-hydroxyeicosanoic acid,2-hydroxydocosanoic acid, 2-hydroxytetracosanoic acid; long chain2-hydroxy branched fatty acids obtained from lanolin and the like;cyclic acids such as cyclohesanoic acid, hydrogenated rosin, rosin,abietic acid, hydrogenated abietic acid, benzoic acid, p-oxybenzoicacid, p-aminobenzoic acid, cinnamic acid, p-methoxycinnamic acid,salicylic acid, gallic acid, pyrrolidonecarboxylic acid, nicotinic acidand the like. Further, naturally-derived fatty acids such as orange oilfatty acid, avocado oil fatty acid, macadamia nut oil fatty acid, oliveoil fatty acid, hydrogenated soy bean oil fatty acid, jojoba oil fattyacid, palm oil fatty acid, hydrogenated palm oil fatty acid, palm kerneloil fatty acid, castor oil fatty acid, wheat germ oil fatty acid,safflower oil fatty acid, turtle oil fatty acid, cotton seed oil fattyacid, beef tallow fatty acid, hydrogenated beef tallow fatty acid,lanolin fatty acid, mink oil fatty acid and the like can also be used inthe present invention since they contain a monocarboxylic acid having 4to 34 carbon atoms.

The dicarboxylic acid used in the present invention is not particularlyrestricted providing it has two or more carboxyl groups in the molecule.Preferable are those represented by the following structural formula 3:HOOC—(CH₂)_(n)—COOH  (3)wherein, n is an integer from 1 to 16, more preferably from 3 to 16.

Examples of the dicarboxylic acid used in the present invention includemalonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid,suberic acid, azelaic acid, sebacic acid, 1,9-nonamethylenedicarboxylicacid, 1,10-decamethylenedicarboxylic acid, 1-,1,1-undecamethylenedicarboxylic acid, 1-, 12-dodecamethylenedicarboxylicacid, 1-13-tridecamethylenedicarboxylic acid, 1-,14-tetradecamethylenedicarboxylic acid,1-,15-hexadecamethylenedicarboxylic acid.

In addition, above described dimer acid usable as a raw material of thedimerdiol can also be used as the dicarboxylic acid to be esterifiedwith the dimerdiol.

The dimerdiol carboxylate of the present invention is obtained, forexample, by esterification of a dimerdiol obtained as described above ortransesterification of a lower alcohol ester thereof with amonocarboxylic acid having 4 to 34 carbon atoms described above or adicarboxylic acid described above.

The esterification conditions are not particularly restricted. Ingeneral, the esterification is conducted by a conventional method.

For example, the esterification can be conducted by using, as acatalyst, p-toluenesulfonic acid, sulfuric acid, hydrochloric acid,methanesulfonic acid, boron trifluoride, hydrogen fluoride and the like,and using, as a solvent, benzene, toluene, hexane, heptane and the like,at 50 to 260° C. Alternatively, the esterification can be conducted withusing neither solvent nor catalyst at 100 to 260° C.

In the transesterification reaction, an alkali catalyst such as sodiumhydroxide, potassium hydroxide, potassium carbonate or the like, or ametal alkoxide such as sodium methoxide, sodium ethoxide, potassiumbutoxide or the like can be used as a catalyst.

In an esterification reaction with a monocarboxylic acid, the averageesterification degree of the resulting ester can be arbitrarilycontrolled from monoester to diester by changing the charging ratio of adimerdiol to a monocarboxylic acid.

The resulting ester may be a diester, a monoester or a mixture thereofdepending on its use. The ester may be a mixture of two or more kinds ofesters with different carboxylic acids. The oil materials of the presentinvention further comprises, in addition to the above esters, an esterwith lower monocarboxylic acid such as acetic acid and propionic acidand/or an ester with a monocarboxylic acid having 34 or more carbonatoms. The oil materials of the present invention comprising thedimerdiol monocarboxylate thus obtained can be used in suitable uses asit is. Alternatively, it can be purified by a usual method, ifnecessary, before being applied to various used.

In an esterification reaction with a dicarboxylilc acid, the averageesterification degree and the average molecular weight of the resultingester can be controlled by changing the charging ratio of a dimerdiol toa dicarboxylic acid.

The charging ratio is preferably from 0.2 to 1.2 mol, more preferablyfrom 0.4 to 1.0, in terms of the molar amount of a dicarboxylic acidbased on the average molecular weight calculated from its acid value per1 mol of a dimerdiol based on the average molecular weight calculatedfrom its hydroxyl value.

The resulting dimerdiol dicarboxylate can have various averageesterification degree and average molecular weight, and may be a mixedester of two or more carboxylic acids, depending on its use. The oilmaterials of the present invention comprising a dimerdiol dicarboxylatethus obtained can be used in suitable uses as it is. Alternatively, itcan be purified by a usual method, if necessary, before being applied tovarious use.

The dimerdiol monocarboxylate and dimerdiol dicarboxylate obtained asdescribed above and oil materials comprising the ester are good inoxidation stability. The oxidation stability can be further improved byadding an antioxidant. As the antioxidant, those usually added to an oilmaterial can be used, and particularly, vitamin E is desirable. Asvitamin E, d-α-tocopherol, d-δ-tocopherol, d,1-α-tocopherol,d-α-tocopherol acetate, d,1-α-tocopherol acetate, tocopherol mixturesseparated and purified from soy bean and rapeseed and the like can beused. The addition amount of the antioxidant is not particularlyrestricted, and suitably from 10 ppm to 10000 ppm based on the amount ofester.

In the esterification with a monocarboxylic acid, esters having arelatively high molecular weight from about 1,000 to 1,300 can beobtained. In spite of the relatively high molecular weight, the oilmaterial has lower viscosity and manifests dry feeling withoutstickiness, causes little skin irritation and has high durability.Further, it has excellent oxidation stability and hydrolysis-resistance,and shows high refractive index and excellent gloss. Further, cosmeticsand external agents comprising such a dimerdiol monocarboxylate areexcellent in safety, hydrolysis-resistance, gloss and feeling of use.

In the esterification reaction with a dicarboxylic acid, a dimerdioldicarboxylate can be obtained in which the weight-average molecularweight by GPC (gel permeation chromatography) analysis is from about2,000 to 20,000. Particularly, when this weight-average molecular weightis from 4,000 to 12,000, it has excellent feeling of use in spite of therelatively high molecular weight and causes little irritation. Further,it has excellent oxidation stability, shows high refractive index andreveals excellent gloss. Still further, cosmetics and external agentscontaining such a dimerdiol dicarboxylate are excellent in safety,stability, pigment dispersability, gloss and feeling of use.

Content of the above dimerdiol ester with a monocarboxylic acid having 4to 34 carbon atoms or a dimerdiol ester with a dicarboxylic acid in theoil material of the present invention is not particularly restricted,although, as a raw material for cosmetics, it is preferably 20% or more,and more preferably 50% or more.

Compounding amount of the dimerdiol ester comprised in the oil materialof the present invention to cosmetics and external agents is notparticularly restricted. Preferably, it is from about 0.1 to 50 wt %,particularly preferably from 0.5 to 30 wt %.

In the cosmetics of the present invention, water, and additives usuallycompounded into cosmetics such as fats and oils, emulsifier, alcohols,humectant, thickening agent, antioxidant, preservative, bactericide,chelating agent, pH regulator, ultraviolet absorber, opacifier, solvent,keratin ablation and resolution agent, antipruritic, antiphlogistine,antiperspirant agent, refrigerant, reductant, antihistamic agent,astringent, stimulant, hair growth agent, polymer powder, hydroxy acid,vitamins and derivatives thereof, saccharides and derivatives thereof,organic acids, enzymes, nucleic acids, hormones, clay minerals,aromatic, coloring agents and the like can be compounded, if necessary.

Examples of the fats and oils include higher alcohols such as cetanol,myristyl alcohol, oleyl alcohol, lauryl alcohol, cetostearyl alcohol,stearyl alcohol, arakyl alcohol, jojoba alcohol, chimyl alcohol, batylalcohol, hexyl alcohol, isostearyl alcohol, 2-octyldodecanol and thelike; lanolins such as liquid lanolin, reduced lanolin, adsorbedpurified lanolin, lanolin acetate, liquid lanolin acetate, hydroxylanolin, polyoxyethylene lanolin, lanolin fatty acid, hard lanolin fattyacid, lanolin alcohol, lanolin alcohol acetate, acetate and the like;phospholipids such as phosphatidyl choline, phosphatidyl ethanolamine,phosphatidyl inositol, sphingomyelin, phosphatidic acid, lysolecithineand the like; phospholipid derivatives such as hydrogenated soy beanphospholipid, hydrogenated yolk phospholipid and the like; sterols suchas cholesterol, dihydrocholesterol, lanosterol, dihydrolanosterol,phytosterol and the like; sterol esters such as cholesteryl acetate,cholesteryl nonanoate, cholesteryl stearate, cholesteryl isostearate,cholesteryl oleate, di(cholesteryl behenyl octyldodecyl)N-lauroyl-L-glutamate, di(cholesteryl.octyldodecyl)N-lauroyl-L-glutamate, di(phytosteryl.2-octyldodecyl)N-lauroyl-L-glutamate, cholesteryl 12-hydroxystearate, cholesterylmacademia nut oil fatty acid ester, phytosteryl macademia nut oil fattyacid ester, phytosteryl isostearate, cholesteryl soft lanolin fatty acidester, cholesteryl hard lanolin fatty acid ester, cholesteryl long chainbranched fatty acid ester, chlesteryl long chain á-hydroxy fatty acidester and the like; lower alcohol fatty acid esters such as ethyloleate, ethyl avocado oil fatty acid ester, isopropyl palmitate, octylpaltitate, isopropyl isostearate, isotridecyl isononanoate, isopropyllanolin fatty acid ester and the like; higher alcohol fatty acid esterssuch as octyldodecyl myristate, cetyl octanoate, oleyl oleate,octyldodecyl oleate, octyldodecyl lanolin fatty acid ester, hexyldecyldimethyloctanoate, dioctyl succinate and the like; higher alcohol oxyacid esters such as cetyl lactate, diisostearyl malate and the like;polyhydric alcohol fatty acid esters such as trioleic glyceride,triisostearic glyceride, tri(capryl.capronic acid) glyceride, dioleicpropylene glycol and the like; silicon resin; dimethicones such asmethylpolysiloxane, octamethyltrisiloxane, decamethyltetrasiloxane,higher polymerized methylpolysiloxane and the like; phenyltrimethiconessuch as methylphenylpolysiloxane and the like; methicones such asmethylhydrogenpolysiloxane and the like; organic modified polysiloxanessuch as laurylmethicone copolyol, dimethiconol stearate, dimethiconecopolyol isostearate and the like; amino modified polysiloxanes such asamodimethicone, amodimethicone copolyol and the like; crosslinked typemethylpolysiloxanes such as crosslinked type methylphenyl polysiloxane,dimethicone/vinyldimethicone cross polymer and the like; anion modifiedpolysiloxanes such as dimethicone copolyol phosphate, dimethiconecopolyol sulfate and the like; alkylfluorodimethicones such asperfluoroethylstearyldimethicone and the like; perfluoro polyether andthe like.

Examples of the emulsified include anionic surfactants such as fattyacid salts, alkylsulfate salts, alkylbenzenesulfonate salts,polyoxyethylenealkylsulfates salts, polyoxyethylene fatty amine sulfatesalt, acyl N-methyltauric acid, alkylether phosphate salt, N-acylaminoacid salt and the like; nonionic surfactants such as polyoxyethylenealkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene alkylether sorbitan fatty acid parital ester, polyhydric alcohol fatty acidpartial ester, polyglycerin fatty acid ester, polyoxyethylene fatty acidester, alkyldimethylamine oxide, alkyl polyglycoside and the like;cationic surfactants such as alkyltrimethylammonium chloride, shortchain polyoxyethylene alkylamine and salts and quaternary salts thereof,benzalconium chloride and the like; amphoteric surfactants such asalkyldimethylaminoacetic acid betaine, alkylamidedimethylaminoaceticacid betaine, 2-alkyl-N-carboxyl-N-hydroxyimidazolinium betaine and thelike; polymer surfactants such as polyvinyl alcohol, sodium alginate,starch derivatives, gum tragacanth, acrylic acid methacryllic acidcopolymer and the like.

Examples of the humectant include polyhydric alcohols such as propyleneglycol, glycerin, 3-methyl-1,3-butane diol and the like; sodiumhyaluronate, citrate salt, urea, lactic acid bacteria culture liqour,yeast extract, egg shell membrane protein, bovine submaxillary salivarygland mucin, hypotaurin, sesame lignan glucoside, betaine, chondroitinsulfate, ceramide (type 1, 2, 3, 4, 5, 6), hydroxyceramide,psuedoceramide, sphingoglucolipid, glutathione, polyethylene glycol,sorbitol, carbitol, sodium lactate, sodium 2-pyrrolidone-5-carboxylate,albumin, trimethylglycine; proteinolyzed peptide and derivatives thereofsuch as collagen, elastin, collagenolyzed peptide, elastinolyzedpeptide, keratinolyzed peptide, conchiolinolyzed peptide, silkproteinolyzed peptide, soy bean protainolyzed peptide, wheatprotainolyzed peptide, caseinolyzed peptide and the like; amino acidssuch as arginine, serine, glycine, threonine, glutamic acid, cisteine,methionine, leucine, tryptophane and the like; animal and vegetableextract components such as placenta extract, elastin, collagen, aloeextract, hamamelis extract, luffa water, chamomile extract, glycyrrhizaextract, black root extract and the like.

Examples of the thickening agent include polymer compounds such as guargum, queens seed gum, xathane gum, carageenan, alginic acid, sodiumcarxobymethylcellulose, carboxyvinylpolymer, polyvinylpyrrolidone,ampholytic methacrylate copolymer, cationized cellulose, polyacrylatecopolymer, nitrocellulose and the like.

Examples of the antioxidant include BHT, BHA, propyl gallate,d-α-tocopherol, d-δ-tocopherol, d,1-α-tocopherol, d-α-tocopherolacetate, d,1-α-tocopherol acetate, and the like.

Examples of the preservative include phenols, benzoic acid and saltsthereof, halogenated bisphenols, acid amides, quarternary ammonium saltsand the like.

Examples of the bactericide include trichlorocarbanide, zinc pyrithione,benzlconium chloride, benzethonium chloride, chlorhexidine, halocarbane,hinokitiol, phenol, isopropylphenol, photosensitive agents and the like.

Examples of the chelating agent include edetate salts, sodium oxalateand the like.

Examples of the pH regulator include citric acid, succinic acid,hydrochloric acid, ethanolamine, diethanolamine, triethanolamine,ammonia water, sodium hydroxide, calcium chloride and the like.

Examples of the ultraviolet absorber include benzophenone derivatives,p-aminobenzoic acid derivatives, p-methoxycinnamic acid derivatives,silicyllic acid derivatives, urocanic acid, urocanate,4-tert-butyl-4′-methoxydibenzoylmethane,2-(2′-hydroxy-5′-methylphenyl)benzotriazole, methyl anthranylate, rutinand derivatives thereof and the like.

Examples of the opacifier include kojic acid, arbutin, ascorbic acid,ascorbic glucoside, glutathione, elagic acid, placenta extract,orizanol, lucinol and the like.

Examples of the solvents include lower alcohols such as ethanol,propanol and the like; acetone, ethylene glycol monomethyl ether,toluene and the like.

Examples of the keratin ablation and resolution agent include salicylicacid, sulfur, resorcin, selenium oxide, pyridoxine and the like.

Examples of antipruritic include diphenhydramine hydrochloride,chlorpheramine maleate, camphor and the like.

Examples of the antiphlogistic agent include glycyrrhizinic acid andderivatives thereof, guaiazulene, hydrocortisone acetate, predonisoneand the like.

Examples of the antiperspirant agent include aluminum hydroxychloride,aluminum chloride, zinc oxide, zinc p-phenolsulfonate and the like.

Examples of the refrigerant include menthol, methyl salicylate and thelike.

Examples of the reductant include thioglycolic acid, cysteine and thelike.

Examples of the antihistamic agent include diphedlamine hydrochloride,chlorphelamine maleate, glycyrrhetinic acid derivatives and the like.

Examples of the astringent include citric acid, tartaricacid, lacticacid, aluminumpotassiumsulfate, tannic acid and the like.

Examples of the stimulant include cantharis tincture, Shoyo tincture,capsicum tincture, benzyl nicotinate and the like.

Examples of the hair growth agent include swertia herb extract,cepharantin, vitamin E and derivatives thereof, ã-orizanol, capsicumtincture, Shoyo tincture, cantharis tincture, benzyl nicotinate,allantoin, photosentive agent 301, photosensitive agent 401 and thelike.

Examples of the polymer powder include starch, nylon powder,polyethylene powder, polymethyl methacrylate, polyethyleneterephthalate, polymethyl methacrylate laminated powder and the like.

Examples of the α-hydroxy acids and derivatives thereof include lacticacid, glycolic acid, fruit acid, hydroxycapric acid, long chainα-hydroxyfatty acid, long chain α-hydroxyfatty acid cholesteryl esterand the like.

Examples of the vitamins and derivatives thereof include vitamins suchas vitamin A, vitamins B, vitamin D, vitamin E, panthotenic acid,biotinic acid and the like; vitamin derivatives such as ascorbylstearate, ascorbyl palmitate, ascorbyl dipalmitate, ascorbyltetraisopalmitate, magnesium ascorbyl phosphate, sodium ascorbate,tocopherol nicotinate, tocopherol acetate, tocopherol linolate,tocopherol ferulate and the like.

Examples of the saccharides and derivatives thereof include saccharidesand derivatives thereof such as cyclodextrin, β-glucan, chithine,chitosan, glucose, trehalose, pectin, arabinogalactan, gelatin, dextrin,dextran and the like.

Examples of the organic acids include abietic acid, tartaric acid andthe like.

Examples of the enzymes include lysozyme chloride, keratinase, papain,pancreatin, protease and the like.

Examples of the nucleic acid include adenosine triphosphate disodium andthe like.

Examples of the hormones include estradiol, estron, ethynylestradiol,cortisone, hydrocortisone, predonizone and the like.

Examples of the clay minerals include montmorillonite, sericite,kaolinite, kaoline and the like.

Examples of the aromatic include limonene, linalool, citral, â-ionone,benzylbenzoate, indol, eugenol, auranthiol, geraniol, liral, damaskon,benzyl acetate, jasmine lactone, galacsolid, essential oil and the like.

Examples of the coloring agent include inorganic pigments such as mica,talk, kaolin, calcium carbonate, red iron oxide, yellow iron oxide,black iron oxide, ultramarine, iron blue, carbon black, titaniumdioxide, zinc oxide, mica titanium, scale foil, boron nitride,photochromic pigment, synthetic fluorine gold mica, fine particlecomplex powder and the like; natural pigments such as β-carotene,calsamine, rutin, cochineal, chlorophyll and the like; organic syntheticcoloring agents such as dyes, lake, organic pigments and the like.

In addition, components used in known cosmetics, medical products, foodand the like can be appropriately compounded within the range in whichthe effect of the present invention does not decrease.

The cosmetic of the present invention can be produced by a usual method.Examples of cosmetics include basic cosmetics, make up cosmetics, haircosmetics, aromatic cosmetics, body cosmetics and the like.

Examples of the basic cosmetics include washing materials such ascleansing foam, cleansing gel, washing powder, cleansing cream,cleansing milk, cleansing lotion, cleansing oil, cleansing mask and thelike; lotions such as softening lotion, astringent lotion, washinglotion, multi-layer lotion and the like; emulsions such as emollientlotion, moisture lotion, milky lotion, nourishing lotion, nourishingmilk, skin moisture, moisture emulsion, massage lotion, cleansinglotion, protect emulsion, sun protect, UV care milk, sun screen, make uplotion, keratin smoother, elbow lotion, hair milk, hand lotion, bodylotion and the like; creams such as emollient cream, nourishing cream,burnishing cream, moisture cream, night cream, massage cream, cleansingcream, make up cream, base cream, pre-make up cream, sun screen cream,san tanning cream, hair remover, hair cream, deodorant cream, shavingcream, keratin softening cream and the like; gels such as cleansing gel,moisture gel and the like: soaps such as cosmetic soap, transparentsoap, medical soap, liquid soap, shaving soap, synthetic cosmetic soapand the like; packs and masks such as peel off pack, powder pack,washing pack, oil pack, cleansing mask and the like; essences such ashumectant essence, opacifying essence, ultraviolet ray preventingessence and the like.

Examples of the make up cosmetics include white powder dustings,foundations: lipsticks such as lipstick, lip gloss, lip cream and thelike, cheek paint, eye liner, mascara, eye shadow, eye brow liner, eyeblow, nail enamel, enamel remover, nail treatment and the like.

Examples of the hair cosmetics include shampoos such as oil shampoo,cream shampoo, conditioning shampoo, dandruff shampoo, rinse-in shampooand the like; rinse; hair grow agent; hair foam, hair moose, hair spray,hair mist, hair gel, water grease, set lotion, color lotion, hairliquid, pomade, tic, hair cream, hair blow, branch coat, hair oil,permanent wave agent, hair dying agent, hair bleach and the like.

Examples of the aromatic cosmetics include aromatic, perfume, perfume,eau de perfume, eau de toilette, eau de cologne, paste aromatic,aromatic powder, aromatic soap, body lotion, bath oil and the like.

Examples of the body cosmetics include body washing materials such asbody shampoo and the like; deodorizing cosmetics such as deodorantlotion, deodorant powder, deodorant spray, deodorant stick and the like;decolorant, dehairing and hair removing; bath additive; insect repellerssuch as insect preventing spray and the like.

Regarding the agent type, emulsion cosmetics in the form of oil in water(O/W) type, water in oil (W/O) type, W/O/W type and O/W/O type, oilycosmetics, solid cosmetics, liquid cosmetics, kneaded cosmetics, stickcosmetics, volatile oily cosmetics, powder cosmetics, jelly cosmetics,gel cosmetics, paste cosmetics, emulsified polymer cosmetics, sheetcosmetics, mist cosmetics, spray cosmetics and the like can be used.

An external agent is directly applied to skin in the form of anointment, patch, lotion, liniment, liquid application agent and thelike. The compounding amount of a dimerdiol ester to the external agentof the present invention is not particularly restricted. Preferably, itis from 0.1 to 50% by weight, particularly preferably from 0.5 to 30 wt%. Additives usually used in ointment, patch, lotion, liniment, liquidapplication agent and the like may be used.

The dimerdiol ester of monocarboxylic acid having 4 to 34 carbon atomscomprised in the oil materials of the present invention is excellent insafety, stability, hydrolysis-resistance, and gloss. Further, it canprovide cosmetics and external agents, comprising the dimerdiolcarboxylate, excellent in safety, stability, hydrolysis-resistance,pigment dispersability, gloss and feeling of use.

The dimerdiol ester with a dicarboxylic acid comprised in the oilmaterials of the present invention is excellent in safety, stability,pigment dispersability, and gloss. Further, it can provide cosmetics andexternal agents, comprising the dimerdiol carboxylate, excellent insafety, stability, pigment dispersability, gloss and feeling of use.

EXAMPLES

The following examples illustrate the present invention in more detail.These examples do not limit the scope of the present invention. Allpercents are by weight unless otherwise stated.

Synthesis Example 1 Production of a Dimerdiol

Into a 500 mL reaction vessel equipped with a stirrer, a thermometer anda gas-introducing tube were charged 140 g of methyl oleate, 60 g ofmethyl linoleate and 15 g of activated clay. After the inner air wasreplaced with nitrogen, the temperature was raised to 240° C. and adimerization reaction was conducted for 6 hours. Then, the activatedclay was removed by filtration and unreacted methyl ester of fatty acidswere removed by distillation to obtain 134 g of dimethyl ester of dimeracids. Into a 500 mL auto clave was charged 125 g of the dimethyl esterof dimer acids thus obtained, and, thereto, 3 g of copper-chromiumcatalyst was added. Then, after the inner air was replaced withhydrogen, a hydrogenation was conducted at a pressure of 250 atmosphere,at 250° C. until no more hydrogen absorption was observed. For removingether compounds and ester compounds, that is impurities, thehydrogenated product was subjected to a molecular distillation to obtain97 g of a dimerdiol as the fraction of distillate at 237-252° C./0.1torr. Acid value and hydroxyl value of the dimerdiol thus obtained were0.2 and 196.0, respectively.

Example 1 Production of a Hydrogenated Rosin Dimerdiol Ester

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 158 g (0.46 mol) of hydrogenatedrosin (KP-610, manufactured by Arakawa Chemical Industries, Ltd.) and134 g (0.23 mol) of the dimerdiol obtained in Synthesis example 1. Afterthe inner air was replaced with nitrogen, the temperature was raised to240° C. and the reaction was conducted for 20 hours under a reducedpressure. After cooling, 160 g of heptane was added thereto andunreacted hydrogenated rosin was removed with an aqueous sodiumhydroxide solution. The resulting mixture was washed with water, andheptane, the solvent in the mixture, was distilled off to obtain 227 gof aimed hydrogenated rosin dimerdiol ester. The obtained hydrogenatedrosin dimerdiol ester is a viscous liquid at a normal temperature, andits acid value and hydroxyl value were 0.7 and 7.0, respectively.

Example 2 Production of a Hydrogenated Rosin Dimerdiol Ester

According to the same manner as in Example 1 except that 100 ppm ofvitamin E (E-mix-D, manufactured by Eisai Co. Ltd.) based on thehydrogenated rosin dimerdiol ester was added after the washing withwater, a tocopherol mixture added hydrogenated rosin dimerdiol ester wasobtained. Analytical values thereof were the same as those in Example 1.

Example 3 Production of a Erucic Acid Dimerdiol Ester

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 160 g (0.46 mol) of erucic acid,128 g (0.22 mol) of the dimerdiol obtained in Synthesis example 1, 1.2 gof para-toluene sulfonic acid and 200 g of heptane, and a dehydrationwas conducted at 110° C. for 7 hours under a nitrogen flow. Aftercooling, unreacted erucic acid was removed with an aqueous sodiumhydroxide solution. The resulting mixture was washed with water, andheptane, the solvent in the mixture, was distilled off to obtain 191 gof aimed erucic acid dimerdiol ester. The obtained erucic acid dimerdiolester is in a liquid state at a normal temperature, and its acid value,hydroxyl value and saponification value were 0.2, 2.1 and 92.8,respectively.

Example 4 Production of a Erucic Acid Dimerdiol Ester

According to the same manner as in Example 3 except that 100 ppm ofd,l-α-tocopherol (manufactured by AJINOMOTO Co. Inc.) based on theerucic acid dimerdiol ester was added after the washing with water, atocopherol mixture added hydrogenated rosin dimerdiol ester wasobtained. Analytical values thereof were the same as those in Example 3.

Example 5 Production of a Mono-Isostearic Acid Dimerdiol Ester

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 94 g (0.33 mol) of isostearicacid, 180 g (0.33 mol) of dimerdiol (PESPOL HP-1000, manufactured byTOAGOSEI Co. Ltd.), 1.2 g of para-toluene sulfonic acid and 150 g ofheptane, and a dehydration was conducted at 110° C. for 6 hours under anitrogen flow. After cooling, unreacted isostearic acid was removed withan aqueous sodium hydroxide solution. The resulting mixture was washedwith water, and heptane, the solvent in the mixture, was distilled offto obtain 221 g of aimed mono-isostearic acid dimerdiol ester. Theobtained mono-isostearic acid dimerdiol ester is in a liquid state at anormal temperature, and its acid value, hydroxyl value andsaponification value were 0.2, 62.1 and 66.5, respectively.

Example 6 Production of a Mono-Isostearic Acid Dimerdiol Ester

According to the same manner as in Example 5 except that 200 ppm ofvitamin E (E-mix-D, manufactured by Eisai Co. Ltd.) based on themono-isostearic acid dimerdiol ester was added after the washing withwater, a tocopherol mixture added mono-isostearic acid dimerdiol esterwas obtained. Analytical values thereof were the same as those inExample 5.

Example 7 Production of a Long Chain Branched Fatty Acid Dimerdiol Ester

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 175 g (0.55 mol) of long chain(Carbon number 10-31) branched fatty acid (FA-NH, manufactured by NipponFine Chemical Co. Ltd.), 159 g (0.28 mol) of dimerdiol (PESPOL HP-1000,manufactured by TOAGOSEI Co. Ltd.), 1.2 g of para-toluene sulfonic acidand 150 g of heptane, and a dehydration was conducted at 110° C. for 7hours under a nitrogen flow. After cooling, unreacted long chainbranched fatty acid was removed with an aqueous sodium hydroxidesolution. The resulting mixture was washed with water, and heptane, thesolvent in the mixture, was distilled off to obtain 261 g of aimed longchain branched fatty acid dimerdiol ester. The obtained long chainbranched fatty acid dimerdiol ester is in a paste state at a normaltemperature, and its acid value, hydroxyl value and saponification valuewere 0.7, 11.6 and 105.1, respectively.

Example 8 Production of a Long Chain Branched Fatty Fatty Acid DimerdiolEster

According to the same manner as in Example 7 except that 300 ppm ofvitamin E (E-mix-D, manufactured by Eisai Co. Ltd.) based on the longchain branched fatty acid dimerdiol ester was added after the washingwith water, a tocopherol mixture added long chain branched fatty aciddimerdiol ester was obtained. Analytical values thereof were the same asthose in Example 7.

Example 9 Production of a Hydrogenated Rosin/Erucic Acid Dimerdiol Ester

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 47 g (0.14 mol) of hydrogenatedrosin (KP-610, manufactured by Arakawa Chemical Industries, Ltd.), 48 g(0.14 mol) of erucic acid, 160 g (0.28 mol) of dimerdiol (PESPOLHP-1000, manufactured by TOAGOSEI Co. Ltd.). After inner air wasreplaced with nitrogen, a dehydration was conducted at 240° C. for 15hours under a nitrogen flow. After cooling, unreacted acids were removedwith an aqueous sodium hydroxide solution. The resulting mixture waswashed with water, and heptane, the solvent in the mixture, wasdistilled off to obtain 225 g of aimed hydrogenated rosin/erucic aciddimerdiol ester. The obtained hydrogenated rosin/erucic acid dimerdiolester is in a liquid state at a normal temperature, and its acid valueand hydroxyl value were 0.1 and 7.6, respectively.

Example 10 Production of a Hydrogenated Rosin/Erucic Acid DimerdiolEster

According to the same manner as in Example 9 except that 300 ppm ofvitamin E (E-mix-D, manufactured by Eisai Co. Ltd.) based on thehydrogenated rosin/erucic acid dimerdiol ester was added after thewashing with water, a tocopherol mixture added hydrogenated rosin/erucicacid dimerdiol ester was obtained. Analytical values thereof were thesame as those in Example 9.

Example 11 Production of a Isostearic Acid Dimerdiol Ester

Into a 2000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 311 g (1.04 mol) of isostearicacid, 287 g (0.52 mol) of dimerdiol (PESPOL HP-1000, manufactured byTOAGOSEI Co. Ltd.), 1.9 g of para-toluene sulfonic acid and 240 g ofheptane, and a dehydration was conducted at 110° C. for 8 hours under anitrogen flow. After cooling, unreacted isostearic acid was removed withan aqueous sodium hydroxide solution. The resulting mixture was washedwith water, and heptane, the solvent in the mixture, was distilled offto obtain 523 g of aimed isostearic acid dimerdiol ester. The obtainedisostearic acid dimerdiol ester is in a liquid state at a normaltemperature, and its acid value, hydroxyl value and saponification valuewere 0.1, 7.1 and 105.5, respectively.

Example 12 Production of a Isostearic Acid Dimerdiol Ester

According to the same manner as in Example 11 except that 500 ppm ofvitamin E (E-mix-D, manufactured by Eisai Co. Ltd.) based on theisostearic acid dimerdiol ester was added after the washing with water,a tocopherol mixture added isostearic acid dimerdiol ester was obtained.Analytical values thereof were the same as those in Example 11.

Reference Example 1

Oxidation stability of the dimerdiol esters obtained in Examples 1-12were measured. Each of the measurement was conducted at 120° C., using 3g of sample, at an air flow rate of 20 L/Hr with a Rancimat 676 typeautomatic oils and fats stability test apparatus (manufactured byShibata/Metrohm Ltd.). Index of the oxidation stability was expressed bythe time until conductance of the trapped water started rising. Theresults are shown in the following table.

TABLE Exam- Index of ple oxidation No. Dimerdiol ester stability 1hydrogenated rosin dimerdiol ester  6 hrs. 2 tocopherol mixture addedhydrogenated 20 hrs. rosin dimerdiol ester 3 erucic acid dimerdiol ester 3 hrs. 4 tocopherol mixture added 27 hrs. erucic acid dimerdiol ester 5mono-isostearic acid dimerdiol ester  8 hrs. 6 tocopherol mixture added48 hrs. mono-isostearic acid dimerdiol ester 7 long chain branched fattyacid dimerdiol  4 hrs. ester 8 tocopherol mixture added long chain 30hrs. branched fatty acid dimerdiol ester 9 hydrogenated rosin/erucicacid  4 hrs. dimerdiol ester 10 tocopherol mixture added hydrogenated 26hrs. rosin/erucic acid dimerdiol ester 11 isostearic acid dimerdiolester  8 hrs. 12 tocopherol mixture added isostearic 48 hrs. or moreacid dimerdiol ester

The results indicate that

any of the tested esters had sufficient oxidation stability to be usedas a raw material for cosmetics, and addition of vitamin E furtherimproves the oxidation stability.

Reference Example 2

Refractive index of the dimerdiol esters obtained in Examples 1, 3, 5,7, 9 and 11 were measured. Each of the refractive index was measured at30° C. using a refractometer Model 3 (Manufactured by ATAGO BUSSANLtd.). The results are shown in the following table.

TABLE Exam- ple Refractive No. Dimerdiol ester index 1 hydrogenatedrosin dimerdiol ester 1.5075 3 erucic acid dimerdiol ester 1.4719 5mono-isostearic acid dimerdiol ester 1.4659 7 long chain branched fattyacid dimerdiol 1.4684 ester 9 hydrogenated rosin/erucic acid 1.4892dimerdiol ester 11 isostearic acid dimerdiol ester 1.4709 PESPOLHP-1000(manufactured by TOAGOSEI 1.4778 Co. Ltd.) liquid lanolinSS(manufactured by 1.4878 Nippon Fine Chemical Co. Ltd.)

The results indicate that

any of the tested esters had refractive index similar to or higher thanthe refractive index of liquid lanolin SS, which is known as an oilmaterial imparting good gloss. Hence, they have good gloss. It can beconsidered that this characteristic is caused by high refractive indexof dimerdiol, the raw material.

Reference Example 3

Alkali hydrolysis resistance of the dimerdiol esters obtained inExamples 1, 3, 5, 7, 9 and 11 were measured. The alkali hydrolysisresistance was expressed by the decomposition ratio of 0.8 g of samplewhich was heated at 80° C. for 3 hours in 25 mL of 0.05 N of KOH-ethanolsolution.

The results are shown in the following table.

TABLE Exam- ple Decomposi- No. Dimerdiol ester tion ratio 1 hydrogenatedrosin dimerdiol ester 3% 3 erucic acid dimerdiol ester 79% 5mono-isostearic acid dimerdiol ester 71% 7 long chain branched fattyacid dimerdiol 73% ester 9 hydrogenated rosin/erucic acid 33% dimerdiolester 11 isostearic acid dimerdiol ester 70% glyceryl isooctanoate 8%(manufactured by Nippon Fine Chemical Co. Ltd.)

The results indicate that

hydrogenated rosin dimerdiol ester exhibited a low decomposition ratioas same as that of glyceryl isooctanoate, which is known as an esterhaving good alkali hydrolysis resistance. Hence, it has good alkalihydrolysis resistance.

Example 13

According to the composition shown in the following Table and accordingto the following manner, an ointment was prepared.

Liquid paraffin, hydrogenated rosin/erucic acid dimerdiol ester obtainedin Example 10, dimethyl siloxane and cetostearyl alcohol were heated upto 70° C. and mixed until a uniform mixture was obtained (oil phase).

Cetrimide and chlorocresol were dissolved in purified water at 70° C. Tothe aqueous solution thus obtained, the oil phase obtained above wasadded with stirring to make a uniform mixture, which was then cooled toroom temperature to obtain an ointment.

TABLE Composition Ingredient % by weight liquid paraffin 30.0hydrogenated rosin/erucic acid dimerdiol 10.0 ester dimethyl siloxane10.0 cetostearyl alcohol 5.0 cetrimide 0.5 chlorocresol 0.1 purifiedwater balance

Comparative Example 1

According to the same manner as in Example 13 except that hydrogenatedrosin/erucic acid dimerdiol ester was replaced with glyceridetristearate, an ointment was prepared.

Example 14

According to the composition shown in the following Table and accordingto the following manner, an emollient cream was prepared.

Dipropylene glycol, glycerin and triethanolamine were dissolved inpurified water, and heated up to 70° C. (water phase). Other ingredientswere mixed at 70° C. (oil phase). To the water phase, the oil phase wasadded slowly with stirring. After stirring further, the obtained mixturewas emulsified with an emulsifier and cooled to room temperature toobtain an emollient cream.

TABLE Composition Ingredient % by weight long chain branched fatty acid7.0 dimerdiol ester obtained in Example 8 stearic acid 3.0 vaseline 6.0cetyl alcohol 5.0 POE(20)-cetyl alcohol ether 2.0 propylene glycolmonostearate 3.0 dipropylene glycol 3.0 glycerine 3.0 triethanolamine1.0 antiseptic, antioxidant q.s. purified water balance

Comparative Example 2

According to the same manner as in Example 14 except that long chainbranched fatty acid dimerdiol ester obtained in Example 8 was replacedwith glyceryl tri-2-ethylhexanate, an emollient cream was prepared.

Example 15

According to the composition shown in the following Table and accordingto the following manner, a milky lotion was prepared.

Polyethylene glycol 1500, 1,3-butyleneglycol and triethanolamine wereadded to purified water, and dissolved by heating up to 70° C. (waterphase). Other ingredients were mixed at 70° C. (oil phase). To the waterphase, the oil phase was added slowly with stirring forpre-emulsification. The resulting mixture was further emulsifieduniformly with an emulsifier and cooled to room temperature to obtain amilky lotion.

TABLE Composition Ingredient % by weight mono-isostearic acid dimerdiolester 3.0 obtained in Example 5 stearic acid 2.0 vaseline 3.0 cetylalcohol 1.0 sorbitan monooleate 2.0 polyethylene glycol 1500 3.01,3-butylene glycol 5.0 triethanolamine 1.0 perfume, preservative q.s.purified water balance

Comparative Example 3

According to the same manner as in Example 15 except thatmono-isostearic acid dimerdiol ester obtained in Example 5 was replacedwith glyceryl tri-2-ethylhexanate, a milky lotion was prepared.

Example 16

According to the composition shown in the following Table and accordingto the following manner, a liquid cream shampoo was prepared.

After purified water was heated up to 70° C., other ingredients wereadded thereto and dissolved uniformly. Then, the resulting mixture wascooled to obtain a liquid cream shampoo.

TABLE Composition Ingredient % by weight long chain branched fatty aciddimerdiol ester 2.0 obtained in Example 8 sodium polyoxyethylene(3)lauryl sulfate(30%) 30.0 sodium lauryl sulfate(30%) 15.0 lauricdiethanolamide 3.0 polyethyleneglycol distearate 2.0 perfume,preservative q.s. sequestering agent, q.s. pH adjusting agent purifiedwater balance

Comparative Example 4

According to the same manner as in Example 16 except that long chainbranched fatty acid dimerdiol ester obtained in Example 8 was replacedwith cetyl 2-ethylhexanate, a liquid cream shampoo was prepared.

Example 17

According to the composition shown in the following Table and accordingto the following manner, a hair conditioner was prepared.

Stearyl trimethylammonium chloride and presevative were dissolved inpurified water by heating up to 70° C. to obtain an aqueous solution.

Erucic acid dimerdiol ester obtained in Example 4, glycerylmonostearate, cetyl alcohol, glycerin and perfume were mixed at 70° C.with stirring. The mixture was added to the aqueous solution obtainedabove, and mixed thoroughly with stirring, followed by cooling toprepare a hair conditioner.

TABLE Composition Ingredient % by weight erucic acid dimerdiol ester 2.0obtained in Example 4 stearyl trimethylammonium chloride 3.0 glycerylmonostearate 0.5 cetyl alcohol 3.0 glycerin 3.0 perfume, preservativeq.s. purified water balance

Comparative Example 5

According to the same manner as in Example 17 except that Erucic aciddimerdiol ester obtained in Example 4 was replaced with beef tallowfatty acid glyceride, a hair conditioner was prepared.

Example 18

According to the composition shown in the following Table and accordingto the following manner, a lipstick was prepared.

Titanium dioxide, Red No. 201 and Red No. 202 were added to a portion ofmono-isostearic acid dimerdiol ester obtained in Example 5. The mixturewas kneaded with a roller and mixed uniformly (pigment portion).

Red No. 223 was dissolved in the remaining mono-isostearic aciddimerdiol ester obtained in Example 5 (dye portion). Other ingredientswere mixed and fused by heating, and, thereto the pigment portion anddye portion were added and dispersed uniformly by a homomixer. Then, thedispersion was put in a mold and cooled rapidly to make a stick.

TABLE Composition Ingredient % by weight hydrogenated rosin dimerdiolester 13.0 obtained in Example 1 trimethylol propane triisostearate 16.0mono-isostearic acid dimerdiol ester 31.0 obtained in Example 5 beeswax9.0 lanolin 6.0 carnauba wax 7.0 ceresine 6.0 hard lanolin fatty acidcholesteryl ester 5.0 titanium dioxide 5.0 Red No.201 0.6 Red No.202 1.2Red No.223 0.2 perfume, preservative q.s.

Comparative Example 6

According to the same manner as in Example 18 except that hydrogenatedrosin dimerdiol ester obtained in Example 1 was replaced withdi-isostearyl malic acid, and mono-isostearic acid dimerdiol esterobtained in Example 5 was replaced with a caster oil, a lipstick wasprepared.

Reference Example 4

Stability at 40° C. of the ointments prepared in Example 13 andComparative example 1, the emollient creams prepared in Example 14 andComparative example 2, the milky lotions prepared in Example 15 andComparative example 3, the shampoos prepared in Example 16 andComparative example 4 and the hair conditioners prepared in Example 17and Comparative example 5 were evaluated. The results according to thefollowing criteria are shown in the following Table.

TABLE Tested Sample stability ointments in Example 13 ◯ emollient creamsin Example 14 ◯ milky lotions in Example 15 ◯ shampoos in Example 16 ◯hair conditioner in Example 17 ◯ ointments in Comparative example 1 Δemollient creams in Comparative example 2 ◯ milky lotions in Comparativeexample 3 Δ shampoos in Comparative example 4 Δ hair conditioner inComparative example 5 ◯ “◯”: Stable even after 30 days from preparation.“Δ”: Phase separation or deposition was observed on 10-29 days afterpreparation. “X”: Phase separation or deposition was observed within 10days after preparation.

The results show that stability of the ointments, milky lotions andshampoos prepared in Examples 13-17 are better than those prepared inComparative examples 1-5.

Reference Example 5

Female panelists were requested to use-test the ointments prepared inExample 13 and Comparative example 1, the emollient creams prepared inExample 14 and Comparative example 2 and the milky lotions prepared inExample 15 and Comparative example 3. The results according to thefollowing criteria are shown in the following table.

TABLE Comparative Examples examples 13 14 15 1 2 3 [Feeling of use]Non-sticky feel ⊚ ⊚ ◯ ◯ ◯ ◯ Dry feeling ◯ ⊚ ⊚ ◯ ◯ ◯ Smooth feel ⊚ ⊚ ⊚ ◯Δ ◯ [Durability] Non-sticky feel ⊚ ⊚ ◯ ◯ ◯ ◯ Dry feeling ◯ ⊚ ⊚ ◯ ◯ ◯Smooth feel ⊚ ⊚ ⊚ ◯ Δ ◯ [Feeling of use] “⊚”: excellent “◯”: good “Δ”:insufficient “X”: bad [Durability]: Feeling of use after used for 5hours “⊚”: excellent “◯”: good “Δ”: insufficient “X”: bad

The results show that Feeling of use and Durability of the ointments,emollient creams and milky lotions of the present invention areexcellent.

Reference Example 6

Female panelists were requested to use-test the shampoos prepared inExample 16 and Comparative example 4 and the hair conditioners preparedin Example 17 and Comparative example 5. Sensory evaluations wereconducted about moist feel, softness, gloss and manageability of hair.The results according to the following criteria are shown in thefollowing table.

TABLE Moist manage- feel Softness gloss ability shampoo of ⊚ ⊚ ⊚ ◯Example 16 hair conditioner ⊚ ⊚ ⊚ ◯ of Example 17 shampoo of Δ ◯ Δ ΔComparative example 4 hair conditioner of Δ ◯ Δ ◯ Comparative example 5[Moist feel] “⊚”: excellent “◯”: good “Δ”: fair “X”: not moist[Softness] “⊚”: very soft “◯”: soft “Δ”: middle of soft and hard “X”:hard [gloss] “⊚”: very gloss “◯”: glossy “Δ”: little glossy “X”: notglossy [manageability] “⊚”: excellent “◯”: good “Δ”: fair “X”: bad

The results show that Feeling of use of the Shampoo and hair conditionerof the present invention are excellent.

Reference Example 7

Female panelists were requested to use-test the lipsticks prepared inExample 18 and Comparative example 6. Sensory evaluations were conductedabout moist feel, adhesiveness, Spreadability, gloss, oxidationstability and perspiration. The results according to the followingcriteria are shown in the following table.

TABLE Lip stick of Lip stick of Comparative [Feeling of use] Example 18example 6 moist feel ⊚ Δ adhesiveness ⊚ Δ spreadability ◯ ◯ gloss ⊚ ΔOxidation ⊚ ◯ stability Perspiration ◯ Δ [Moist feel] “⊚”: excellent“◯”: good “Δ”: fair “X”: not moist [Adhesiveness] “⊚”: excellent “◯”:good “Δ”: in-between good and bad “X”: bad [Spreadability] “⊚”:excellent “◯”: good “Δ”: in-between good and bad “X”: bad [gloss] ⊚”:very glossy “◯”: glossy “Δ”: little glossy “X”: not glossy [oxidationstability] Change of odor was evaluated after leaving in an oven at 40°C. for 3 months. “◯”: No change was observed. “X”: A clear change wasobserved. [perspiration] “◯”: No perspiration was observed for 2 monthsor longer. “Δ”: No perspiration was observed for 2 weeks or longer. “X”:Perspiration was observed within 2 weeks.

The results show that the lipstick of the present invention areexcellent in Feeling of use and perspires little.

Examples 19-27

Compounding dimerdiol esters of the present invention, foundations,sunscreen agents, mascara, eye shadows and lipsticks were produced. Allproducts exhibited good stability and usability. The formulas andprocesses for the productions are shown below.

Example 19 Powdery Foundation

Composition No. Ingredient % by weight 1. talc 15.0 2. mica 30.0 3.kaolin 15.0 4. titanium dioxide 15.0 5. titanated mica 3.0 6. zincstearate 1.0 7. nylon powder 5.0 8. red iron oxide 1.0 9. yellow ironoxide 3.0 10. black iron oxide 0.2 11. squalane 6.0 12. hydrogenatedrosin dimerdiol ester 1.0 obtained in Example 2 13. octyldodecylmyristate 2.0 14. neopentylglycol diisooctanoate 2.0 15. sorbitanmonooleate 0.5 16. preservative q.s. 17. antioxidant q.s. 18. perfumeq.s.

Above ingredients No. 1 and No. 8-10 were mixed with henshel type mixer.Then, ingredients 2-7 were added thereto and mixed thoroughly. Theresulting mixture and a mixture which was prepared by mixing ingredients12-18 with heating to 70° C. were mixed and crushed to obtain aimedpowdery foundation.

Example 20 Milky Foundation

Composition No. Ingredient % by weight 1. ion-exchanged water 60.9 2.dispersant 0.1 3. dipropylene glycol 5.0 4. preservative q.s. 5.polyoxyethylene modified 4.0 dimethylpolysiloxane 6.decamethylcyclopentasiloxane 12.0 7. isostearic acid dimerdiol ester 5.0obtained in Example 12 8. zinc white 10.0 9. sericite 0.36 10. titaniumdioxide 8.32 11. yellow iron oxide 0.80 12. red iron oxide 0.36 13.black iron oxide 0.16 14. perfume q.s.

Above ingredients No. 1-4 were mixed with heating, and, thereto,ingredients No. 9-13 were added and dispersed. Then, the resulting washeated to 70° C. and mixed with ingredients 5-7, followed by carryingout emulsification. Then, the emulsified mixture was cooled to roomtemperature and, thereto, ingredient 14 was added to obtain aimed milkyfoundation.

Example 21 Dual-Use Foundation

Composition No. Ingredient % by weight 1. silicon treated talc 19.0 2.silicon treated mica 40.0 3. silicon treated titanium dioxide 5.0 4.zinc white 15.0 5. silicon treated red iron oxide 1.0 6. silicon treatedyellow iron oxide 3.0 7. silicon treated black iron oxide 0.2 8. zincstearate 0.1 9. nylon powder 2.0 10. monoisostearic acid dimerdiol ester4.0 obtained in Example 6 11. solid paraffin 0.5 12. dimethylpolysiloxane 4.0 13. glyceryl triisooctaonate 5.0 14. octylmethoxycinnamate 1.0 15. preservative q.s. 16. antioxidant q.s. 17.perfume q.s.

Above ingredients No. 1-9 were mixed with henshel type mixer. Then, theresulting mixture and a mixture which was prepared by mixing ingredients10-17 with heating to 70° C. were mixed and crushed to obtain aimedfoundation.

Example 22 Oily Stick Foundation

Composition No. Ingredient % by weight 1. talc 15.0 2. titanium oxide7.0 3. kaolin 20.0 4. mica 3.3 5. red iron oxide 1.0 6. yellow ironoxide 3.0 7. black iron oxide 0.2 8. solid paraffin 3.0 9. microcrystaline wax 7.0 10. vaseline 14.0 11. phytosteryl/isostearyldimerdilinoleate 1.0 (PHY/IS-DA, manufactured by Nippon Fine ChemicalCo. Ltd.) 12. dimethyl polysiloxane 3.0 13. monoisostearic aciddimerdiol ester 5.0 obtained in Example 6 14. isopropyl palmitate 17.015. antioxidant q.s. 16. perfume q.s.

Above ingredients No. 8-15 were mixed at 85° C., and ingredients No. 1-7were added thereto, mixed by a disper and dispersed with a colloid mill.Ingredient 16 was added to the resulting mixture, and, after beingde-gassed, the mixture was poured to a vessel at 70° C. and cooled.

Example 23 Sunscreen Agent

Composition No. Ingredient % by weight 1. ultra fine particle titaniumoxide 5.0 2. ion-exchanged water 54.95 3. 1,3-butylene glycol 7.0 4.EDTA-2Na 0.05 5. triethanolamine 1.0 6. oxybenzone 2.0 7. octylparamethoxycinnamate 5.0 8. squalane 9.0 9. long chain branched fattyacid 5.0 dimerdiol ester obtained in Example 8 10.phytosteryl/isostearyl dimerdilinoleate 1.0 (PHY/IS-DA, manufactured byNippon Fine Chemical Co. Ltd.) 11. stearyl alcohol 3.0 12. stearic acid3.0 13. glyceryl monostearate 3.0 14. polyethylacrylate 1.0 15.preservative q.s. 16. antioxidant q.s. 17. perfume q.s.

Above ingredients No. 2-5 were mixed at 70° C., and ingredients No. 1was added thereto and dispersed thoroughly. Then, the resulting mixtureand a mixture which was prepared by mixing ingredients 6-17 with heatingwere mixed and emulsified with a homogenizer. Thereafter, the resultingwas cooled with stirring to obtain aimed sunscreen agent.

Example 24 Mascara

Composition No. Ingredient % by weight 1. black iron oxide 10.0 2.hydrogenated rosin dimerdiol ester 20.0 obtained in Example 2 3.polyacrylic acid ester emulsion 20.0 4. solid paraffin 8.0 5. lanolinwax 8.0 6. light isoparaffin 17.0 7. sorbitan sesquioleate 3.0 8.purified water 10.0 9. 2-ethylhexyl-p-cinnamate 3.0 10. preservativeq.s. 11. perfume q.s.

Oily ingredients No. 2-7, 9, 10 and 11 were mixed with heating. (oilpart) To the oil part, ingredient 1 was added and dispersion treatmentwas conducted. Then, heated ingredient 8 was added to the oil part, andfurther dispersion treatment, then cooling, were conducted to obtainaimed mascara.

Example 25 Milky Eye Shadow

Composition No. Ingredient % by weight 1. talc 10.0  2. kaolin 4.0 3.pigment 5.0 4. hydrogenated rosin dimerdiol ester 17.0  obtained inExample 2 5. phytosteryl/isostearyl dimerdilinoleate 3.0 (PHY/IS-DA,manufactured by Nippon Fine Chemical Co. Ltd.) 6. stearic acid 7.0 7.isopropyl myristate 1.0 8. liquid paraffin 4.0 9. propylene glycolmonolaurate 1.5 10. antioxidant q.s. 11. perfume q.s. 12. purified water45.0  13. butylene glycol 5.0 14. light isoparaffin 1.0 15.2-ethylhexyl-p-cinnamate 5.0 16. preservative q.s. 17. triethanol amine1.0 18. sequestering agent q.s.

Above ingredients No. 4-9 and 16 were mixed with heating to 70° C., andingredients No. 14 and 15 were added thereto. (oil part) Ingredients 13,17 and 18 were dissolved in ingredient 12, and ingredients 1, 2 and 3were added thereto, thoroughly dispersed and heated to 70-80° C. (waterpart)

Then, the water part was added to the oil part and emulsified. Using anemulsifier, emulsified particles were adjusted, and cooling andde-gassing were conducted to obtain aimed milky eye shadow.

Example 26 Lipstick

Composition Ingredient % by weight 1. ceresine 5.0 2. paraffin wax 10.03. candelira wax 3.0 4. carnauba wax 2.0 5. lanolin fatty acidcholesteryl ester 5.0 (YOFCO CLE-S, manufactured by Nippon Fine ChemicalCo. Ltd.) 6. phytosteryl/isostearyl dimerdilinoleate 1.0 (PHY/IS-DA,manufactured by Nippon Fine Chemical Co. Ltd.) 7. isostearic aciddimerdiol ester 15.0 obtained in Example 11 8. mono-isostearic aciddimerdiol ester 28.8 obtained in Example 5 9. polyether modifiedsilicone 10.0 10. perfluoro polyether (FOMBLIN HC-04) 5.0 11. red No.201 1.0 12. red No. 202 2.0 13. yellow No. 4 A1 lake 1.0 14. titaniumoxide 1.0 15. lecithin 0.5 16. vitamin A 0.5 17. antioxidant 0.1 18.perfume 0.1

Ingredients 11-14 were added to a portion of ingredient 7 and kneadedwith a roller to make the mixture uniform. After adding otheringredients thereto, mixing by heating, the mixture was poured to a moldand cooled rapidly to obtain aimed lipstick.

Example 27 Lipgloss

Composition Ingredient % by weight 1. dextrin palmitate 10.0 2.hydrogenated rosin dimerdiol ester 30.0 obtained in Example 1 3.macadamia nut oil fatty acid cholesteryl ester 10.0 (YOFCO MAC,manufactured by Nippon Fine Chemical C. Ltd.) 4. phytosteryl/isostearyldimerdilinoleate 10.0 (PHY/IS-DA, manufactured by Nippon Fine ChemicalCo. Ltd.) 5. methyl phenyl polysiloxane 30.0 6. glyceryltri-2-ethylhexanoate 5.0 7. liquid paraffin 5.0

Whole ingredients were heated, fused and mixed. Then, the mixture waspoured in a vessel, then, cooled and solidified to obtain aimedlipgloss.

Example 28 Production of an Ester of Dimerdiol and Dimer Acid

Into a 500 mL reaction vessel equipped with a stirrer, a thermometer anda gas-introducing tube were charged 75 g (0.1364 mol) of dimerdiol(PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.) and 39.1 g (0.0682mol) of dimer acid (Empol 1061, manufactured by Henkel Co. Ltd.). Afterinner air was replaced with nitrogen, the temperature was raised to 220°C. and an esterification was conducted at 220-230° C. for 6 hours undera nitrogen flow and reduced pressure (133-220 hPa). 107.7 g of aimeddimerdiol/dimer acid ester was obtained. Hereinafter, this ester isreferred to as “DD-DA/1:0.5”. The ester properties of DD-DA/1:0.5 are asfollows.

acid value: 1.44,

hydroxyl value: 70.8,

saponification value: 72.5

Mn*: 2,600, Mw*: 5,200 Hereinafter, Mn and Mw indicate number averagemolecular weight and weight average molecular weight measured by Gelpermeation chromatography (GPC).

Example 29 Production of an Ester of Dimerdiol and Dimer Acid

Into a 500 mL reaction vessel equipped with a stirrer, a thermometer anda gas-introducing tube were charged 60.0 g (0.109 mol) of dimerdiol(PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.) and 43.8 g (0.0764mol) of dimer acid (Empol 1061, manufactured by Henkel Co. Ltd.). Afterinner air was replaced with nitrogen, the temperature was raised to 220°C. and an esterification was conducted at 220-230° C. for 6 hours undera nitrogen flow and reduced pressure (133-220 hPa). To the resultingproduct, 300 ppm of vitamin E (E-mix-D, manufactured by Eisai Co. Ltd.All vitamin E used in the Examples and Comparative examples below arethe same as that used in this Example.) was added to obtain 95.7 g ofaimed dimerdiol/dimer acid ester. Hereinafter, this ester is referred toas “DD-DA/1:0.7”. The ester properties of DD-DA/1:0.7 are as follows.

acid value: 1.62,

hydroxyl value: 39.3,

saponification value: 86.4

Mn: 3,400, Mw: 9,500

Example 30 Production of an Ester of Dimerdiol and Hydrogenated DimerAcid

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 250.0 g (0.455 mol) of dimerdiol(PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.) and 130.8 g (0.227mol) of dimer acid (Empol 1008, manufactured by Henkel Co. Ltd.). Afterinner air was replaced with nitrogen, the temperature was raised to 220°C. and an esterification was conducted at 220-230° C. for 6 hours undera nitrogen flow and reduced pressure (133-213 hPa). To the resultingproduct, 300 ppm of vitamin E was added to obtain 362.9 g of aimeddimerdiol/dimer acid ester. Hereinafter, this ester is referred to as“DD-HDA/1:0.5”. The ester properties of DD-HDA/1:0.5 are as follows.

acid value: 1.09,

hydroxyl value: 65.5,

saponification value: 57.7

Mn: 2,500, Mw: 4,900

Example 31 Production of an Ester of Dimerdiol and Hydrogenated DimerAcid

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 200.0 g (0.364 mol) of dimerdiol(PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.) and 146.5 g (0.255mol) of dimer acid (Empol 1008, manufactured by Henkel Co. Ltd.). Afterinner air was replaced with nitrogen, the temperature was raised to 220°C. and an esterification was conducted at 220-230° C. for 6 hours undera nitrogen flow and reduced pressure (133-213 hPa). To the resultingproduct, 300 ppm of vitamin E was added to obtain 327.2 g of aimeddimerdiol/dimer acid ester. Hereinafter, this ester is referred to as“DD-HDA/1:0.7”. The ester properties of DD-HDA/1:0.7 are as follows.

acid value: 1.37,

hydroxyl value: 33.9,

saponification value: 86.4

Mn: 3,800, Mw: 8,200

Example 32 Production of an Ester of Dimerdiol and Hydrogenated DimerAcid

Into a 2000 mL reaction vessel equipped with a stirrer, a thermometer, agas-introducing tube and a reflux condenser were charged 200.0 g (0.364mol) of dimerdiol (PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.),146.5 g (0.255 mol) of dimer acid (Empol 1008, manufactured by HenkelCo. Ltd.), 350 ml of n-heptane and 3.5 g of para-toluene sulfonic acid,as a catalyst. The mixture was heated up to 110-115° C., and thereaction was conducted for 8 hours under nitrogen flow, while heatingand refluxing the solvent and distilling out the produced water. Then,the resulting mixture was cooled to 70-80° C., and treated with alkali,the amount being more than that required for neutralizing the catalyst.After washing with water for deacidification, removing the solvent underreduced pressure, successively, 300 ppm of vitamin E was added theretoto obtain 330.3 g of aimed dimerdiol/dimer acid ester. Hereinafter, thisester is referred to as “DD-HDAS/1:0.7”. The ester properties ofDD-HDAS/1:0.7 are as follows.

acid value: 0.3,

hydroxyl value: 33.0,

saponification value: 85.2

Mn: 3,700, Mw: 8,000

Example 33 Production of an Ester of Dimerdiol and Sebacic Acid

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 280.0 g (0.509 mol) of dimerdiol(PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.) and 51.6 g (0.255mol) of sebacic acid (manufactured by KOKURA SYNTHETIC INDUSTRIES,Ltd.). After inner air was replaced with nitrogen, the temperature wasraised to 220° C. and an esterification was conducted at 220-230° C. for5 hours under a nitrogen flow and reduced pressure (133-213 hPa). To theresulting product, 300 ppm of vitamin E was added to obtain 308.1 g ofaimed dimerdiol/sebacic acid ester. Hereinafter, this ester is referredto as “DD-SEBA/1:0.5”. The ester properties of DD-SEBA/1:0.5 are asfollows.

acid value: 1.34,

hydroxyl value: 92.7,

saponification value: 77.1

Mn: 1,600, Mw: 3,300

Example 34 Production of an Ester of Dimerdiol and Sebacic Acid

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometerand a gas-introducing tube were charged 250.0 g (0.455 mol) of dimerdiol(PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.) and 64.5 g (0.318mol) of sebacic acid (manufactured by KOKURA SYNTHETIC INDUSTRIES,Ltd.). After inner air was replaced with nitrogen, the temperature wasraised to 220° C. and an esterification was conducted at 220-230° C. for5 hours under a nitrogen flow and reduced pressure (133-213 hPa). To theresulting product, 300 ppm of vitamin E was added to obtain 288.8 g ofaimed dimerdiol/sebacic acid ester. Hereinafter, this ester is referredto as “DD-SEBA/1:0.7”. The ester properties of DD-SEBA/1:0.7 are asfollows.

acid value: 1.48,

hydroxyl value: 58.0,

saponification value: 128.8

Mn: 2,200, Mw: 5,500

Example 35 Production of an Ester of Dimerdiol and Hydrogenated DimerAcid

Into a 2000 mL reaction vessel equipped with a stirrer, a thermometer, agas-introducing tube and a reflux condenser were charged 200.0 g (0.364mol) of dimerdiol (PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.),51.6 g (0.255 mol) of sebacic acid (manufactured by KOKURA SYNTHETICINDUSTRIES, Ltd.), 350 ml of n-heptane and 3.5 g of para-toluenesulfonic acid, as a catalyst. The mixture was heated up to 110-115° C.,and the reaction was conducted for 8 hours under nitrogen flow, whileheating and refluxing the solvent and distilling out the produced water.Then, the resulting mixture was cooled to 70-80° C., and treated withalkali, the amount being more than that required for neutralizing thecatalyst. After washing with water for deacidification, removing thesolvent under reduced pressure, successively, 300 ppm of vitamin E wasadded thereto to obtain 220.0 g of aimed dimerdiol/sebacic acid ester.Hereinafter, this ester is referred to as “DD-SEBAS/1:0.7”. The esterproperties of DD-SEBAS/1:0.7 are as follows.

acid value: 0.3,

hydroxyl value: 60.3,

saponification value: 125.0

Mn: 2,100, Mw: 3,300

Reference Example 8

Oxidation stability of the esters obtained in Examples 28-35 weremeasured. Each of the measurement was conducted at 120° C., using 3 g ofsample, at an air flow rate of 20 L/Hr with a Rancimat 676 typeautomatic oils and fats stability test apparatus (manufactured byShibata/Metrohm Ltd.). Index of the oxidation stability was expressed bythe time until conductance of the trapped water started rising. Theresults are shown in the following table.

TABLE Example Index of oxi- No. Ester dation stability 28 DD-DA/1:0.5 10hrs. 29 DD-DA/1:0.7 15 hrs. 30 DD-HDA/1:0.5 14 hrs. 31 DD-HDA/1:0.7 20hrs. 32 DD-HDAS/1:0.7 21 hrs. 33 DD-SEBA/1:0.5 15 hrs. 34 DD-SEBA/1:0.723 hrs. 35 DD-SEBAS/1:0.7 25 hrs.

The results indicate that

any of the tested esters of the present invention were stable more than10 hours, and had sufficient oxidation stability.

Reference Example 9

Refractive index of the esters obtained in Examples 28-35 were measured.Each of the refractive index was measured at 20° C. using arefractometer Model 3 (Manufactured by ATAGO BUSSAN Ltd.). The resultsare shown in the following table.

TABLE Example Refractive No. Ester index 28 DD-DA/1:0.5 1.4867 29DD-DA/1:0.7 1.4876 30 DD-HDA/1:0.5 1.4844 31 DD-HDA/1:0.7 1.4848 32DD-HDAS/1:0.7 1.4846 33 DD-SEBA/1:0.5 1.4830 34 DD-SEBA/1:0.7 1.4833 35DD-SEBAS/1:0.7 1.4835 liquid lanolin SS (manufactured by Nippon Fine1.4930 Chemical Co. Ltd.) di-iostearyl malate (manufactured by NissinOil 1.4611 Mills Ltd.)

The results indicate that

any of the tested esters of the present invention had refractive indexsimilar to the refractive index of liquid lanolin SS, which is known asan oil imparting good gloss. Hence, they have good gloss.

Reference Example 10

Dispersability for pigment, titanium dioxide, red iron oxide and organicpigment Red No. 202, of the esters obtained in Examples 28-35,polybutene (PARLEAM 18, manufactured by NOF CORP.) and di-isostearylmalate (Cosmol 222, manufactured by Nissin Oil Mills Ltd.) weremeasured. Titanium dioxide, red iron oxide and organic pigment used inthe measurement are PIGMOLITE CR-50, PIGMOLITE BENGARA No. 211 and Red202, respectively, manufactured by DAITO KASEI KOGYO Co. Ltd. Thedispersability is expressed by amount (g) of the tested sample per 100 gof the pigment at wet point (W.P) and flow point (F.P).

TABLE Titanium Red iron dioxide oxide Red 202 Ester W.P F.P W.P F.P W.PF.P DD-DA/1:0.5 45 97 69 224 120 165 DD-DA/1:0.7 66 86 76 172 140 175DD-HDA/1:0.5 57 105 70 230 119 163 DD-HDA/1:0.7 64 114 80 193 142 177DD-HDAS/1:0.7 66 117 75 200 138 170 DD-SEBA/1:0.5 44 97 73 252 105 156DD-SEBA/1:0.7 66 95 75 229 117 149 DD-SEBAS/1:0.7 63 98 78 210 148 150Ester obtained in 53 83 71 195 123 172 Example 2 Ester obtained in 29 8261 168  95 188 Example 6 polybutene 55 100 68 236 116 198 di-iostearyl26 55 63 188 106 200 malate

The results indicate that

any of the tested esters of the present invention are superior indispersability for titanium dioxide to polybutene, and superior indispersability for red iron oxide to polybutene and di-iostearyl malate.

Reference Example 11

Esters obtained in Examples 28-35, liquid lanolin (YOFCO Liquid lanolinSS, manufactured by Nippon Fine Chemical Co. Ltd.), polybutene (HV-100F,manufactured by Nippon Oil Co. Ltd.) and di-iostearyl malate (Cosmol222, manufactured by Nissin Oil Mills Ltd.) were solidified bycompounding 20% of ceresine or candelira wax.

Each of the solidified product was coated on paraffin paper and glosswas measured with a handy glossmeter manufactured by HORIBA Ltd. Glosswas expressed by intensity of light reflected on the coated surface ofparaffin paper at incident angle/reflection angle of 60°.

TABLE Gloss Ester Ceresin Candelira wax DD-DA/1:0.5 60 61 DD-DA/1:0.7 5961 DD-HDA/1:0.5 63 61 DD-HDA/1:0.7 64 61 DD-HDAS/1:0.7 63 61DD-SEBA/1:0.5 63 58 DD-SEBA/1:0.7 64 57 DD-SEBAS/1:0.7 64 58 liquidlanolin 66 64 polybutene 45 48 di-iostearyl 35 41 malate

The results indicate that

gloss of any of the tested esters of the present invention are almostthe same as gloss of liquid lanolin, and much higher than gloss ofpolybutene and di-iostearyl malate.

Example 36

According to the composition shown in the following Table and accordingto the following manner, an ointment was prepared.

Liquid paraffin, DD-DA/1:0.5 obtained in Example 28, dimethyl siloxaneand cetostearyl alcohol were heated up to 70° C. and mixed until auniform mixture was obtained (oil phase).

Cetrimide and chlorocresol were dissolved in purified water at 70° C. Tothe aqueous solution thus obtained, the oil phase obtained above wasadded with stirring to make a uniform mixture, which was then cooled toroom temperature to obtain an ointment.

TABLE Composition Ingredient % by weight liquid paraffin 30.0 DD-DA/1:0.5 10.0  dimethyl siloxane 10.0  cetostearyl alcohol 5.0cetrimide 0.5 chlorocresol 0.1 purified water balance

Example 37

According to the same manner as in Example 36 except that DD-DA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, an ointment wasprepared.

Comparative Example 7

According to the same manner as in Example 36 except that DD-DA/1:0.5was replaced with glyceride tristearate, an ointment was prepared.

Example 38

According to the composition shown in the following Table and accordingto the following manner, an emollient cream was prepared.

Dipropylene glycol, glycerin and triethanolamine were dissolved inpurified water, and heated up to 70° C. (water phase). Other ingredientswere mixed and fused at 70° C. (oil phase). To the water phase, the oilphase was added slowly with stirring. After stirring further, theobtained mixture was emulsified with an emulsifier and cooled to roomtemperature to obtain an emollient cream.

TABLE Composition Ingredient % by weight DD-HDA/1:0.5 obtained inExample 30 3.0 Sorbitan monostearate 3.0 stearic acid 3.0 vaseline 6.0cetyl alcohol 5.0 POE(20)-cetyl alcohol ether 2.0 propylene glycolmonostearate 3.0 dipropylene glycol 3.0 glycerine 3.0 triethanolamine1.0 antiseptic, antioxidant q.s. purified water balance

Example 39

According to the same manner as in Example 38 except that DD-HDA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, an emollientcream was prepared.

Comparative Example 8

According to the same manner as in Example 38 except that DD-HDA/1:0.5was replaced with glyceryl tri-2-ethylhexanate, an emollient cream wasprepared.

Example 40

According to the composition shown in the following Table and accordingto the following manner, a milky lotion was prepared.

Polyethylene glycol 1500, 1,3-butyleneglycol and triethanolamine wereadded to purified water, and dissolved by heating up to 70° C. (waterphase). Other ingredients were mixed and fused at 70° C. (oil phase). Tothe water phase, the oil phase was added slowly with stirring forpre-emulsification. The resulting mixture was further emulsifieduniformly with an emulsifier and cooled to room temperature to obtain amilky lotion.

TABLE Composition Ingredient % by weight DD-HDA/1:0.5 obtained inExample 30 3.0 stearic acid 2.0 vaseline 3.0 cetyl alcohol 1.0 sorbitanmonooleate 2.0 polyethylene glycol 1500 3.0 1,3-butylene glycol 5.0triethanolamine 1.0 perfume, preservative q.s. purified water balance

Example 41

According to the same manner as in Example 40 except that DD-HDA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, a milky lotionwas prepared.

Comparative Example 9

According to the same manner as in Example 40 except that DD-HDA/1:0.5was replaced with glyceryl tri-2-ethylhexanate, a milky lotion wasprepared.

Example 42

According to the composition shown in the following Table and accordingto the following manner, a liquid cream shampoo was prepared.

After purified water was heated up to 70° C., other ingredients wereadded thereto and dissolved uniformly. Then, the resulting mixture wascooled to obtain a liquid cream shampoo.

TABLE Composition Ingredient % by weight DD-HDA/1:0.5 obtained inExample 30 2.0 sodium polyoxyethylene(3) lauryl sulfate(30%) 30.0 sodium laurylsulfate(30%) 15.0  lauric diethanolamide 3.0polyethyleneglycol distearate 2.0 perfume, preservative q.s.sequestering agent and q.s. pH adjusting agent purified water balancebalance

Example 43

According to the same manner as in Example 42 except that DD-HDA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, a liquid creamshampoo was prepared.

Comparative Example 10

According to the same manner as in Example 42 except that DD-HDA/1:0.5was replaced with cetyl 2-ethylhexanate, a liquid cream shampoo wasprepared.

Example 44

According to the composition shown in the following Table and accordingto the following manner, a hair conditioner was prepared.

Stearyl trimethylammonium chloride and presevative were dissolved inpurified water by heating up to 70° C. to obtain an aqueous solution.

DD-HDA/1:0.7 obtained in Example 31, glyceryl monostearate, cetylalcohol, glycerin and perfume were mixed at 70° C. with stirring. Themixture was added to the aqueous solution obtained above, and mixedthoroughly with stirring, followed by cooling to prepare a hairconditioner.

TABLE Composition Ingredient % by weight DD-HDA/1:0.7 obtained inExample 31 2.0 stearyl trimethylammonium chloride 3.0 glycerylmonostearate 0.5 cetyl alcohol 3.0 glycerin 3.0 perfume, preservativeq.s. purified water balance

Example 45

According to the same manner as in Example 44 except that DD-HDA/1:0.7was replaced with DD-SEBA/1:0.7 obtained in Example 34, a hairconditioner was prepared.

Comparative Example 11

According to the same manner as in Example 44 except that DD-HDA/1:0.5was replaced with beef tallow fatty acid glyceride, a hair conditionerwas prepared.

Example 46

Using DD-HDA/1:0.5 obtained in Example 30 and according to thecomposition shown in the following Table, a rinse was prepared.

TABLE Composition Ingredient % by weight silicone oil 3.0 liquidparaffin 1.0 DD-HDA/1:0.5 obtained in Example 30 1.0 cetyl alcohol 1.5stearyl alcohol 1.0 stearyl trimethylammonium chloride 3.0 glycerin 3.0perfume q.s. coloring agent q.s. preservative q.s. purified waterbalance

Example 47

According to the same manner as in Example 46 except that DD-HDA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, a rinse wasprepared.

Comparative Example 12

According to the same manner as in Example 46 except that DD-HDA/1:0.5was replaced with di-isostearyl malate, a rinse was prepared.

Example 48

Titanium dioxide, Red No. 201 and Red No. 202 were added to a portion ofDD-DA/1:0.7 obtained in Example 29. The mixture was kneaded with aroller and mixed uniformly (pigment portion).

Red No. 223 was dissolved in the remaining DD-DA/1:0.7 obtained inExample 29 (dye portion). Other ingredients were mixed and fused byheating, and, thereto the pigment portion and dye portion were added anddispersed uniformly by a homomixer. Then, the dispersion was put in amold and cooled rapidly to make a stick.

TABLE Composition Ingredient % by weight DD-DA/1:0.7 obtained in Example29 30.0 diglyceryl triisostearyate 14.0 trimethylol propanetriisostearate 16.0 beewax 9.0 lanolin 6.0 carnauba wax 7.0 ceresine 6.0hard lanolin fatty acid cholesteryl ester 5.0 titanium dioxide 5.0 RedNo.201 0.6 Red No.202 1.2 Red No.223 0.2 perfume, preservative q.s.

Example 49

According to the same manner as in Example 48 except that DD-DA/1:0.7was replaced with DD-SEBA 1:0.7 obtained in Example 34, a lipstick wasprepared.

Comparative Example 13

According to the same manner as in Example 48 except that DD-DA/1:0.7was replaced with di-isostearyl malic acid (Cosmol 222, manufactured byNissin Oil Mills Ltd.), a lipstick was prepared.

Example 50

According to the same manner as in Example 48 except that DD-DA/1:0.7was replaced with DD-HDA/1:0.7 obtained in Example 31, a lipstick wasprepared.

Example 51

According to the same manner as in Example 50 except that DD-HDA/1:0.7was replaced with DD-SEBAS/1:0.7 obtained in Example 35, a lipstick wasprepared.

Comparative Example 14

According to the same manner as in Example 50 except that DD-HDA/1:0.7was replaced with polybutene (PARLEAM 18, manufactured by NOF CORP.), alipstick was prepared.

Example 52 Lipgloss

Composition No. Ingredient % by weight 1. dextrin palmitate 10.0 2.DD-HDAS/1:0.7 obtained in Example 32 30.0 3. macadamia nut oil fattyacid cholesteryl ester 10.0 4. methyl phenyl polysiloxane 30.0 5.glyceryl tri-2-ethyl hexanate 5.0 6. liquid paraffin 15.0

Whole ingredients were heated, fused and mixed. Then, the mixture waspoured in a vessel, then, cooled and solidified to obtain aimedlipgloss.

Example 53

According to the same manner as in Example 52 except that DD-HDAS/1:0.7was replaced with DD-SEBAS/1:0.7 obtained in Example 35, a lipgloss wasprepared.

Comparative Example 15

According to the same manner as in Example 52 except that DD-HDAS/1:0.7was replaced with polybutene (PARLEAM 18, manufactured by NOF CORP.), alipgloss was prepared.

Example 54 Powdery Foundation

Composition No. Ingredient % by weight 1. talc 15.0 2. mica 30.0 3.kaolin 15.0 4. titanium dioxide 15.0 5. titanated mica 3.0 6. zincstearate 1.0 7. nylon powder 5.0 8. red iron oxide 1.0 9. yellow ironoxide 3.0 10. black iron oxide 0.2 11. squalane 6.0 12. DD-DA/1:0.7obtained in Example 29 1.0 13. octyldodecyl myristate 2.0 14.neopentylglycol diisooctanate 2.0 15. sorbitan monooleate 0.5 16.preservative q.s. 17. antioxidant q.s. 18. perfume q.s.

Above ingredients No. 1 and No. 8-10 were mixed with henshel type mixer.Then, ingredients 2-7 were added thereto and mixed thoroughly. Theresulting mixture and a mixture which was prepared by mixing ingredients12-18 with heating to 70° C. and fusing were mixed and crushed to obtainaimed powdery foundation.

Example 55

According to the same manner as in Example 54 except that DD-DA/1:0.7was replaced with DD-SEBA/1:0.7 obtained in Example 34, a powderyfoundation was prepared.

Comparative Example 16

According to the same manner as in Example 54 except that DD-DA/1:0.7was replaced with diisostearyl malate, a powdery foundation wasprepared.

Example 56 Milky Foundation

Composition No. Ingredient % by weight 1. ion-exchanged water 60.9 2.dispersant 0.1 3. propylene glycol 5.0 4. preservative q.s. 5.polyoxyethylene modified 4.0 dimethylpolysiloxane 6.decamethylcyclopentasiloxane 12.0 7. DD-HDA/1:0.7 obtained in Example 345.0 8. zinc white 10.0 9. sericite 0.36 10. titanium dioxide 8.32 11.yellow iron oxide 0.80 12. red iron oxide 0.36 13. black iron oxide 0.1614. perfume q.s.

Above ingredients No. 1-4 were mixed with heating, and, thereto,ingredients No. 9-13 were added and dispersed. Then, the resulting washeated to 70° C. and mixed with ingredients 5-7, followed by carryingout emulsification. Then, the emulsified mixture was cooled to roomtemperature and, thereto, ingredient 14 was added to obtain aimed milkyfoundation.

Example 57

According to the same manner as in Example 56 except that DD-HDA/1:0.7was replaced with DD-SEBA/1:0.7 obtained in Example 34, a milkyfoundation was prepared.

Comparative Example 17

According to the same manner as in Example 56 except that DD-HDA/1:0.7was replaced with diisostearyl malate, a milky foundation was prepared.

Example 58 Foundation

Composition No. Ingredient % by weight 1. silicon treated talc 19.0 2.silicon treated mica 40.0 3. silicon treated titanium dioxide 5.0 4.zinc white 15.0 5. silicon treated red iron oxide 1.0 6. silicon treatedyellow iron oxide 3.0 7. silicon treated black iron oxide 0.2 8. zincstearate 0.1 9. nylon powder 2.0 10. DD-DA/1:0.5 obtained in Example 284.0 11. solid paraffin 0.5 12. dimethyl polysiloxane 4.0 13. glyceryltriisooctanate 5.0 14. octylmethoxy cinnamte 1.0 15. preservative q.s.16. antioxidant q.s. 17. perfume q.s.

Above ingredients No. 1-9 were mixed with henshel type mixer. Then, theresulting mixture and a mixture which was prepared by mixing ingredients10-17 with heating to 70° C. and fusing were mixed and crushed to obtainaimed foundation.

Example 59

According to the same manner as in Example 58 except that DD-DA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, a foundation wasprepared.

Comparative Example 18

According to the same manner as in Example 56 except that DD-DA/1:0.5was replaced with diisostearyl malate, a foundation was prepared.

Example 60 Oily Stick Foundation

Composition No. Ingredient % by weight 1. talc 15.0 2. titanium oxide7.0 3. kaolin 20.0 4. mica 3.3 5. red iron oxide . 1.0 6. yellow ironoxide 3.0 7. black iron oxide 0.2 8. solid paraffin 3.0 9. microcrystaline wax 7.0 10. vaseline 15.0 11. dimethyl polysiloxane 3.0 12.DD-HDAS/1:0.7 obtained in Example 32 5.0 13. isopropyl palmitate 17.014. antioxidant q.s. 15. perfume q.s.

Above ingredients No. 8-14 were mixed and fused at 85° C., andingredients No. 1-7 were added thereto, mixed by a disper and dispersedwith a colloid mill. Ingredient 15 was added to the resulting mixture,and, after being de-gassed, the mixture was poured to a vessel at 70° C.and cooled.

Example 61

According to the same manner as in Example 60 except that DD-HDAS/1:0.7was replaced with DD-SEBAS/1:0.7 obtained in Example 35, an oily stickfoundation was prepared.

Comparative Example 19

According to the same manner as in Example 56 except that DD-HDAS/1:0.7was replaced with polybutene (PARLEAM 18, manufactured by NOF CORP.) anoily stick foundation was prepared.

Example 62 Sunscreen Agent

Composition No. Ingredient % by weight 1. ultra fine particle titaniumoxide 5.0 2. ion-exchanged water 54.95 3. 1,3-butylene glycol 7.0 4.EDTA-2Na 0.05 5. triethanolamine 1.0 6. oxybenzone 2.0 7. octylparamethoxycinnamete 5.0 8. squalane 10.0 9. DD-HDA/1:0.5 obtained inExample 30 5.0 10. stearyl alcohol 3.0 11. stearic acid 3.0 12. glycerylmonostearate 3.0 13. ethyl polyacrylate 1.0 14. preservative q.s. 15.antioxidant q.s. 16. perfume q.s.

Above ingredients No. 2-5 were mixed and fused at 70° C., andingredients No. 1 was added thereto and dispersed thoroughly. Then, theresulting mixture and a mixture which was prepared by mixing ingredients6-16 with heating and fusing were mixed and emulsified with ahomogenizer. Thereafter, the resulting was cooled with stirring toobtain aimed sunscreen agent.

Example 63

According to the same manner as in Example 62 except that DD-HDA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, a sunscreenagent was prepared.

Comparative Example 20

According to the same manner as in Example 62 except that DD-HDA/1:0.5was replaced with polybutene (PARLEAM 18, manufactured by NOF CORP.), asunscreen agent was prepared.

Example 64 Mascara

Composition No. Ingredient % by weight 1. black iron oxide 10.0 2.DD-DA/1:0.7 obtained in Example 29 20.0 3. polyacrylic acid esteremulsion 20.0 4. solid paraffin 8.0 5. lanolin wax 8.0 6. lightisoparaffin 17.0 7. sorbitan sesquioleate 3.0 8. purified water 10.0 9.2-ethylhexyl-p-cinnamate 3.0 10. preservative q.s. 11. perfume q.s.

Oily ingredients No. 2-7, 9, 10 and 11 were mixed with heating andfusing. (oil part) To the oil part, ingredient 1 was added anddispersion treatment was conducted. Then, heated ingredient 8 was addedto the oil part, and further dispersion treatment, then cooling, wereconducted to obtain aimed mascara.

Example 65

According to the same manner as in Example 64 except that DD-DA/1:0.7was replaced with DD-SEBA/1:0.7 obtained in Example 34, a mascara wasprepared.

Comparative Example 21

According to the same manner as in Example 64 except that DD-DA/1:0.7was replaced with polybutene (PARLEAM 18, manufactured by NOF CORP.), amascara was prepared.

Example 66 Milky Eye Shadow

Composition No. Ingredient % by weight 1. talc 10.0 2. kaolin 4.0 3.pigment 5.0 4. DD-DA/1:0.5 obtained in Example 28 20.0 5. stearic acid7.0 6. isopropyl myristate 1.0 7. liquid paraffin 4.0 8. propyleneglycol monolaurate 1.5 9. antioxidant q.s. 10. perfume q.s. 11. purifiedwater 45.0 12. butylene glycol 5.0 14. light isoparaffin 1.0 15.2-ethylhexyl-p-cinnamate 5.0 16. preservative q.s. 17. triethanol amine1.0 18. sequestering agent q.s.

Above ingredients No. 4-8 and 15 were mixed with heating to 70° C. andfusing, and ingredients No. 13 and 14 were added thereto. (oil part)

Ingredients 12, 16 and 17 were dissolved in ingredient 11, andingredients 1, 2 and 3 were added thereto, thoroughly dispersed andheated to 70-80° C. (water part)

Then, the water part was added to the oil part and emulsified. Using anemulsifier, emulsified particles were adjusted, and cooling andde-gassing were conducted to obtain aimed milky eye shadow.

Example 67

According to the same manner as in Example 66 except that DD-DA/1:0.5was replaced with DD-SEBA/1:0.5 obtained in Example 33, a milky eyeshadow was prepared.

Comparative Example 22

According to the same manner as in Example 66 except that DD-DA/1:0.5was replaced with polybutene (PARLEAM 18, manufactured by NOF CORP.), amilky eye shadow was prepared.

Reference Example 12

Stability at 40° C. of the ointment, lip stick, emollient cream,shampoo, rinse, hair conditioner, milky lotion, powdery foundation,milky foundation, dual-use-foundation, oily stick foundation, sunscreenagent, mascara, milky eye shadow and lipgloss prepared in Examples 36-67and those prepared in Comparative examples 7-22 were evaluated. Theresults according to the following criteria are shown in the followingTable.

TABLE Tested Sample stability ointment of Example 36 ◯ ointment ofExample 37 ◯ emollient cream of Example 38 ◯ emollient cream of Example39 ◯ milky lotion of Example 40 ◯ milky lotion of Example 41 ◯ liquidcreamshampoo of Example 42 ◯ liquid creamshampoo of Example 43 ◯ hairconditioner of Example 44 ◯ hair conditioner of Example 45 ◯ rinse ofExample 46 ◯ rinse of Example 47 ◯ lipstick of Example 48 ◯ lipstick ofExample 49 ◯ lipstick of Example 50 ◯ lipstick of Example 51 ◯ lipglossof Example 52 ◯ lipgloss of Example 53 ◯ powdery foundation of Example54 ◯ powdery foundation of Example 55 ◯ milky foundation of Example 56 ◯milky foundation of Example 57 ◯ dual-use foundation of Example 58 ◯dual-use foundation of Example 59 ◯ oily stick foundation of Example 60◯ oily stick foundation of Example 61 ◯ sunscreen agent of Example 62 ◯sunscreen agent of Example 63 ◯ mascara of Example 64 ◯ mascara ofExample 65 ◯ milky eye shadow of Example 66 ◯ milky eye shadow ofExample 67 ◯ ointment of CP Example 7 ◯ (hereinafter CP Exampleindicates Comparative Example) emollient cream of CP Example 8 ◯ milkylotion of CP Example 9 Δ liquid creamshampoo of CP Example 10 ◯ hairconditioner of CP Example 11 Δ rinse of CP Example 12 Δ lipstick of CPExample 13 ◯ lipstick of CP Example 14 ◯ lipgloss of CP Example 15 ◯powdery foundation of CP Example 16 ◯ milky foundation of CP Example 17◯ dual-use foundation of CP Example 18 ◯ oily stick foundation of CPExample 19 ◯ sunscreen agent of CP Example 20 Δ mascara of CP Example 21◯ milky eye shadow of CP Example 22 ◯ “◯”: Stable even after 30 daysfrom preparation. “Δ”: Phase separation or deposition was observed on10-29 days after preparation. “X”: Phase separation or deposition wasobserved within 10 days

The results show that stability of the milky lotion, hair conditioner,rinse and sunscreen agent prepared in Examples are better than thoseprepared in Comparative examples.

Reference Example 13

Female panelists were requested to use-test the ointments prepared inExamples 36 and 37 and Comparative example 7, the emollient creamsprepared in Examples 38 and 39 and Comparative example 8 and the milkylotions prepared in Examples 40 and 41 and Comparative example 9. Theresults according to the following criteria are shown in the followingtable.

TABLE Feeling of use Durability Non- dry Non- dry sticky feel- smoothsticky feel- smooth feel ing feel feel ing feel ointment of ⊚ ◯ ⊚ ⊚ ◯ ⊚Example 36 ointment of ⊚ ◯ ⊚ ◯ ◯ ⊚ Example 37 emollient cream ⊚ ◯ ◯ ⊚ ◯⊚ of Example 38 emollient cream ◯ ◯ ⊚ ◯ ◯ ⊚ of Example 39 milky lotion ⊚⊚ ⊚ ⊚ ⊚ ⊚ of Example 40 milky lotion ◯ ◯ ⊚ ◯ ◯ ⊚ of Example 41 ointmentof ◯ ◯ ◯ ◯ ◯ ◯ CP example 7 emollient cream ◯ Δ Δ ◯ Δ Δ of CP example 8milky lotion of ◯ Δ Δ ◯ Δ Δ CP example 9 [Feeling of use] “⊚”: excellent“◯”: good “Δ”: insufficient “X”: bad [Durability]: Feeling of use afterused for 5 hours “⊚“: excellent “◯”: good “Δ”: insufficient “X”: bad

The results show that Feeling of use and Durability of the ointments,emollient creams and milky lotions of the present invention areexcellent.

Reference Example 14

Female panelists were requested to use-test the shampoos prepared inExample 42 and 43 and Comparative example 10, the hair conditionersprepared in Examples 44 and 45 and Comparative example 11 and rinsesprepared in Examples 46 and 46 and Comparative example 12. Sensoryevaluations were conducted about moist feel, softness, gloss andmanageability of hair. The results according to the following criteriaare shown in the following table.

TABLE Moist manage- feel Softness gloss ability shampoo of ◯ ⊚ ⊚ ◯Example 42 shampoo of ◯ ◯ ◯ Δ Example 43 hair conditioner ◯ ⊚ ⊚ ◯ ofExample 44 hair conditioner ◯ ◯ ⊚ ◯ of Example 45 rinse of ◯ ⊚ ⊚ ◯Example 46 rinse of ◯ ◯ ◯ ◯ Example 47 shampoo of ◯ ◯ Δ Δ CP example 10hair conditioner of Δ ◯ Δ ◯ CP example 11 rinse of CP example 12 Δ Δ ◯ Δ[Moist feel] “⊚”: excellent “◯”: good “Δ” : fair “X”: not moist[Softness] “◯”: very soft “◯”: soft “Δ”: middle of soft and hard “X”:hard [gloss] “◯”: very glossy “◯”: glossy “Δ”: little glossy “X”: notglossy [manageability] “◯”: excellent “◯”: good “Δ”: fair “X”: bad

The results show that feeling of use of the shampoo, hair conditionerand rinse of the present invention are excellent.

Reference Example 15

Female panelists were requested to use-test the lipsticks prepared inExamples 48-51 and Comparative example 13-14 and the lipgloss preparedin Examples 52 and 53 and Comparative example 15. Sensory evaluationswere conducted about moist feel, adhesiveness, spreadability, gloss,oxidation stability and perspiration. The results according to thefollowing criteria are shown in the following table.

TABLE Feeling of use moist adhesi- spread- feel veness ability glosslipstick of ◯ ⊚ ◯ ⊚ Example 48 lipstick of ◯ ⊚ ◯ ⊚ Example 49 lipstickof ◯ ⊚ ◯ ⊚ Example 50 lipstick of ◯ ⊚ ◯ ⊚ Example 51 lipgloss of ◯ ⊚ ◯ ⊚Example 52 lipgloss of ◯ ⊚ ◯ ⊚ Example 53 lipstick of ◯ ◯ ◯ ◯ CP Example13 lipstick of Δ ◯ Δ ◯ CP Example 14 lipgloss of Δ ◯ Δ ◯ CP Example 15oxidation stability perspiration lipstick of ◯ ◯ Example 48 lipstick of◯ ◯ Example 49 lipstick of ◯ ◯ Example 50 lipstick of ◯ ◯ Example 51lipgloss of ◯ ◯ Example 52 lipgloss of ◯ ◯ Example 53 lipstick of Δ ◯ CPExample 13 lipstick of ◯ Δ CP Example 14 lipgloss of Δ Δ CP Example 15[Moist feel] “⊚”: excellent “◯”: good “Δ”: fair “X”: not moist[adhesiveness] “⊚”: excellent “◯”: good “Δ”: in-between good and bad“X”: bad [spreadability] “⊚”: excellent “◯”: good “Δ”: in-between goodand bad “X”: bad [gloss] “⊚”: very glossy “◯”: glossy “Δ”: little glossy“X”: not glossy [oxidation stability] Change of odor was evaluated afterleaving in an oven at 40° C. for 3 months. “◯”: Almost no change wasobserved. “X”: A clear change was observed. [perspiration] “◯”: Noperspiration was observed for 2 months or longer. “Δ”: No perspirationwas observed for 2 weeks or longer. “X”: Perspiration was observedwithin 2 weeks.

The results show that the lipstick and lipgloss of the present inventionare excellent in feeling of use, oxidation stability and perspirationpreventing property.

Reference Example 16

Female panelists were requested to use-test the powdery foundationprepared in Examples 54 and 55 and Comparative example 16, the milkyfoundation prepared in Examples 56 and 57 and Comparative example 17,the dual-use foundation prepared in Examples 58 and 59 and Comparativeexample 18, and the oily stick foundation prepared in Examples 60 and 61and Comparative example 19. Sensory evaluations were conducted aboutmoist feel, adhesiveness, spreadability, smoothness and oxidationstability. The results according to the following criteria are shown inthe following table.

TABLE Feeling of use moist adhesi- spread- oxidation feel veness abilitygloss stability powdery foundation ◯ ⊚ ⊚ ◯ ⊚ of Example 54 powderyfoundation ◯ ⊚ ⊚ ⊚ ◯ of Example 55 milky foundation of ◯ ⊚ ◯ ◯ ⊚ Example56 milky foundation of ◯ ⊚ ◯ ⊚ ⊚ Example 57 dual-use foundation ◯ ⊚ ◯ ⊚⊚ of Example 58 dual-use foundation ◯ ◯ ◯ ⊚ ◯ of Example 59 oily stick ◯⊚ ⊚ ◯ ⊚ foundation of Example 60 oily stick ◯ ⊚ ⊚ ◯ ◯ foundation ofExample 61 powdery foundation ◯ ◯ ◯ ◯ ◯ of CP Example 16 milkyfoundation of Δ ◯ Δ ◯ ◯ CP Example 17 dual-use foundation ◯ ◯ ◯ ◯ ◯ ofCP Example 18 oily stick Δ ⊚ ◯ Δ ⊚ foundation of CP Example 19 [Moistfeel] “⊚”: excellent “◯”: good “Δ”: fair “X”: not moist [adhesiveness]“⊚”: excellent “◯”: good “Δ”: in-between good and bad “X”: bad[spreadability] “⊚”: excellent “◯”: good “Δ”: in-between good and bad“X”: bad [smoothness] “⊚”: very smooth “◯”: smooth “X”: not smooth[oxidation stability] Change of odor was evaluated after leaving in anoven at 40° C. for 3 months. “⊚”: Almost no change was observed. “◯”: Alittle change was observed, but usable level. “X”: A clear change wasobserved.

The results show that the foundations of the present invention are goodin feeling of use and oxidation.

1. A cosmetic or an external agent comprising a dimerdiol ester of amonocarboxylic acid having 10 to 32 carbon atoms and/or a dimerdiolester of a dicarboxylic acid, wherein said dimerdiol is a dimerdiolproduced by hydrogenating a dimer acid obtained by dimerization of anunsaturated fatty acid having 11 to 22 carbon atoms.
 2. The cosmetic oran external agent according to claim 1, wherein the amount of thedimerdiol ester is 0.1-50% by weight in the cosmetic or external agent.3. The cosmetic or an external agent according to claim 1, wherein thedimerdiol ester is of a dicarboxylic acid.
 4. The cosmetic or anexternal agent according to claim 3, wherein the dicarboxylic acidcomprises an acid represented by the following structural formula 3:HOOC—(CH₂)_(n)—COOH  (3) wherein n is an integer from 1 to
 16. 5. Thecosmetic or an external agent according to claim 3, wherein thedicarboxylic acid comprises a dimer acid.
 6. The cosmetic or an externalagent according to claim 3, wherein the dimerdiol ester is obtained byall esterification reaction of a dimerdiol with a dicarboxylic acidwherein the charging ratio is from 0.2 to 1.2 mol in terms of the molaramount of a dicarboxylic acid based on the average molecular weightcalculated from its acid value per 1 mol of a dimerdiol based on theaverage molecular weight calculated from its hydroxyl value.
 7. Thecosmetic or an external agent according to claim 3, wherein theweight-average molecular weight of the dimerdiol ester is from 4000 to12000.
 8. The cosmetic or an external agent according to claim 1, whichfurther comprises an antioxidant.
 9. The cosmetic or an external agentaccording to claim 8, wherein the antioxidant is vitamin E.
 10. Acosmetic or an external agent comprising a dimerdiol ester of amonocarboxylic acid selected from the group consisting of: i) linearsaturated acids having 4 to 34 carbon atoms, ii) branched fatty acidshaving 4 to 34 carbon atoms, iii) linear unsaturated acids having 10 to32 carbon atoms, iv) hydroxy acids having 4 to 34 carbon atoms and v)cyclic acids having 4 to 34 carbon atoms, selected from the groupconsisting of cyclohexanoic acid, hydrogenated rosin, rosin, abieticacid, hydrogenated abietic acid, benzoic acid, p-oxybenzoic acid,p-aminobenzoic acid, salicylic acid, gallic acid, pyrrolidonecarboxylicacid and nicotinic acid; and/or a dimerdiol ester of a dicarboxylicacid, and wherein said dimerdiol is a dimerdiol produced byhydrogenating a dimer acid obtained by dimerization of an unsaturatedfatty acid having 11 to 22 carbon atoms.
 11. The cosmetic or an externalagent according to claim 10, wherein the dimerdiol ester is of amonocarboxylic acid having 10 to 32 carbon atoms.
 12. The cosmetic or anexternal agent according to claim 11, wherein the monocarboxylic acidcomprises a branched fatty acid.
 13. The cosmetic or an external agentaccording to claim 11, wherein the monocarboxylic acid comprises alinear unsaturated fatty acid having 10 to 32 carbon atoms.
 14. Thecosmetic or an external agent according to claim 11, wherein themonocarboxylic acid comprises a rosin or a hydrogenated rosin.